Search results for: 'fmoc acid'

Game Changer for Protein Modification: Discover oxidation-induced furan crosslinking and 5-hydroxy-1,5-dihydro-2H-pyrrol-2-ones ( 5HP2O s) as stable alternative to maleimides.

We expanded our portfolio of Fmoc-protected homo amino acids . Benefit of their unique properties to modulate the stability, hydrophobicity, and biological performance of your peptide!

Discover MYTsA as coupling reagent for peptide synthesis in “traditional” C→N and vice versa in “natural” N→C direction. Avoid racemization and benefit of improved atom economy!

Tetrahydropyranyl (THP) is an excellent protective group for hydroxy and thiol moieties but rarely used in solid-phase peptide synthesis (SPPS). Discover its advantages, e.g., over O/S t Bu and Trt.

Collect information about the most common side reactions during Fmoc SPPS and how to avoid them! Choose your building blocks and conditions wisely to avoid unnecessary trouble!

Discover the diversity of TentaGel® Resins ! Read our blog to get more information about our latest product additions and possible applications and find the right resin for your research endeavors!

Cyclophase Synthesis - Dissolve. React. Precipitate. Filter. Repeat! Make your peptide synthesis greener by avoiding DMF and benefit from the advantages of both liquid and solid phase synthesis.

Mix & Match. Discover typically employed protecting groups used to temporarily mask reactive functional moieties during solid-phase peptide synthesis to prevent undesired side-reactions.

Shaken, not stirred. Amino-Li resin – a cross-linked polyacrylic amide solid support suitable for the synthesis of peptides and biomolecules, which is compatible with organic as well as aqueous solvents.

Get the most out of your synthesis! Monitor your deprotection and coupling steps for completion and optimize your reaction protocols to maximize yields and minimize side-products! 

Wondering about the difference between Boc and Fmoc chemistry in solid phase peptide synthesis? Don't worry: in this short overview we will guide you through the basics of both strategies.

Discover photocages – photosensitive protecting groups that are removed by irradiation with light of a defined wavelength, thus restoring the original, “active” state.

Have an additional ace up your sleeve for selective and efficient peptide modification, cyclization, and/or bioconjugation. Explore 2-cyanopyridines for click-like reactions. Get more information!

Engineer shape-shifting peptides , controllable by a laser as magic wand! In this newsletter, we’ll explore the possibilities of photo switchable building blocks based on azobenzene.

You are looking for monodisperse Sarcosines ? You want to use Sarcosine for SPPS? You need to improve your drug's hydrophilicity and search for PEG alternatives? Read on!

You missed our workshop featuring Dr. Fabio de Moliner & Prof. Dr. Marc Vendrell? Watch the Recording! Any further questions? Please get in contact via info@iris-biotech.de.

Explore phenylisopropylesters (OPP/OPis) as carboxy protecting groups. Facilitate your peptide synthesis with building blocks for precise side chain modifications or seamless macrolactamizations. 

You are looking for a building block suitable to control the folding characteristics of your peptide or want to add a pH-sensitive conformational switch? Discover aminoprolines and their properties!

Live-imaging of dynamic structures and catching events in living cells is a challenge, as most fluorescent probes have a high background signal. For alternatives, please read on!

The tetrazole isostere of malonyllysine is thermally stable and does not suffer from decarboxylation. Discover our building blocks suitable for incorporation via solid-phase peptide synthesis.

Our special Christmas offer is still valid! Get our standard L-amino acid bundle with 30% discount compared to standard prices. Choose your packaging unit!

Curious about the highlights of our 2023 portfolio additions? Discover innovative building blocks and latest technologies! Read on to check out the summary or get in contact if you need more details!

Do not miss our special Christmas offer starting on December 1st!

Add glycans to your proteins with our ready-to-use Fmoc asparagine building blocks suitable for solid phase peptide synthesis and produce peptides with exactly defined glycosylation patterns!

The discovery of the Merrifield peptide synthesis paved the way for automated solid-phase peptide synthesis (SPPS) enabling fast and convenient simultaneous peptide synthesis.

Discover our small-sized, neutral Fmoc-protected nitrobenzoselenadiazole- and nitrobenzothiadiazole-modified amino acids suitable for SPPS of fluorescent peptides. 

One molecule, two identities: PNAs are composed of nucleobases arranged on a peptidic backbone. Discover our PNA building blocks as ready-to-use bases suitable for SPPS.

Sick of Lysine side chain protecting groups jumping around, yielding scrambled peptides? Check our various options to fine-tune protecting group stability vs. cleavability to optimize your peptide yield.

Ongoing research efforts lead to the discovery of innovative building blocks and new APIs. However, for industrial applications, upscaling is required. Herein, we share the process development for Fmoc-Cys(Msbh)-OH.

Discover the cyanobenzothiazole (CBT) click reaction , a not (yet) so well-known biocompatible and bio-orthogonal mechanism faster than the famous azide-alkyne cycloaddition (CuAAC).

Curious about our latest portfolio additions from January to June 2023? Discover our New Products Flyer and check out the summary of recent product highlights! Get in contact for more details!

Add a new dimension of orthogonality to your peptide synthesis by using Safety-Catch arylalkyl sulfoxide protecting groups! This newsletter tells you about benefits and usage – Read on!

Our building block Fmoc-L-Cys(Cam)-OH enables peptides resembling reduced and carbamido-methylated protein fragments by standard SPPS without error-prone modification reactions.

Peptide therapeutics – fewer injections/lower doses by prolonging their half-life via addition of a lipid modification that promotes binding to serum proteins such as albumin. Read on for recent innovations!

Non-canonical Tryptophan analogs can help to improve your API’s performance in terms of potency, specificity, and stability. We offer various substituted Trp derivatives also available in small quantities for screening.

Argpyrimidine is the result of a Maillard Reaction-like nonenzymatic posttranslational modification. You want to investigate the effect of this change on function and stability? Get the building block!

In two joint studies together with Prof. F. Albericio we investigated the coupling efficiencies of Ser and Thr pseudoproline monomers and their use for the synthesis of inaccessible peptide sequenes. Read on!

Herein we investigate the incorporation of the Fmoc-Thr-pseudoproline monomer during Fmoc SPPS. Typically, pseudoprolines are incorporated as preformed dipeptides. However, the possibility of using the monomer adds flexibility to the synthesis.

We can’t get enough of new products and innovations! Read this blog to get detailed information on the cyanylating reagent NTCB as well as selenocysteine amino acids, both useful tools for peptide ligation.

You are working on complex peptides and are looking for a new level of orthogonality facilitating the overall synthetic process and improving your yields? Check out the Msbh safety-catch protecting group!

From mg synthesis of a peptide up to bulk quantities often makes a huge difference in the route of production. Read on for more information about Iris Biotech’s process development services.

Read on for detailed information on the results of our comparative study on different methods to tackle aspartimide formation. Click here!

Herein, we report the first-time SPPS of a special peptide sequence via employment of of a serine pseudoproline building block as well as sec-isamyl mercaptan (SIT) as cysteine protecting group.

You want to get an overview about the various resins available at Iris Biotech as well as their specifications, differences, and applications? Read on for further information and details.

The Dawson Linker and its variants provide access to C-terminal peptide thioesters which are crucial components of Native Chemical Ligation reactions. Read on to discover all derivatives available at Iris Biotech!

The para -azido benzyloxycarbonyl protected lysine building block Fmoc-L-Lys(4-N3-Z)-OH (FAA8830) is useful for a wide range of applications. Read on to find out more!

For selected products we added minimum purity and minimum enantiomeric purity as part of our product description on our website. High product qualities at Iris Biotech – Read on for more info.

Replace undesired solvents such as DCM, THF and DMF during the loading of 2-CTC and 4-MBH-Br resin by a “greener” EtOAc/MeCN (1:1) mixture. Click here and read on for more details.

We are providing variously functionalized, protected and unprotected fatty acid derivatives suitable for SPPS and further conjugation, e.g. via Click chemistry. Read on to discover our portfolio.

Interested in the introduction of Sarcosine (N-methylglycine), e.g. for hydrophilicity increase of your derivative of choice or for PEG replacement? Check-out our available Sarcosine building blocks!

Discover our selection of propargyl-substituted amino acids and find the best position for subsequent Click chemistry within your peptide/protein. Just click here for further information on our products.

Looking for an acid stable protecting group? Struggling with undesired loss of the Cbz protecting group while removing Boc under acidic conditions? Read on to find out more about iNoc as alternative.

Herein, we summarize certain product highlights and innovations, which we presented in our newsletters 2021. Have a look and get in contact for more information or an individualized offer.

Herein we present a series of alpha,alpha-cycle-disubstituted amino acid derivatives used in peptide design for their structure promoting effects as well as conformational rigidity.

Typically known and employed as preformed dipeptides, we are presenting Serine- and Threonine-derived Pseudoproline monomers as building blocks for solid-phase peptide synthesis.

Check out our growing portfolio on adamantyl-substituted amino acids and building blocks. At Iris Biotech, we are constantly striving to improve our services, our products, and the routes of synthesis.

Back in the lab after enjoying your holidays? Motivated to run new experiments but lacking certain building blocks or standards? Check out our huge portfolio or get in contact for our special offers!

Discover the versatile applications of hydrazone resins e.g. for the preparation of peptide hydrazides, or the generation of peptide thio esters. Read on to find out more and see our available products.

You missed our workshop featuring Prof. Dr. Jeffrey W. Bode (ETH Zurich)? Any further questions? Please get in contact via info@iris-biotech.de

Selenocysteine (Sec) plays a crucial role for various biological processes, and selenoproteins can be found in all lineages of life. Read on to discover the 21 st amino acid, its derivatives and applications.

Herein we are presenting 2-(Fmoc-amino)-3,3-diMe-pent-4-enoic acid (FAA5040), a protease stable Ile/Leu surrogate suitable for further modification via its side chain double bond.

Aspartimide formation remains one major hurdle during peptide synthesis. Read on to find out more about different strategies and available products at Iris Biotech in order to avoid this side product.

Compounds of the shown formula can simply be bound to solid supports via amide bond formation without racemization of the C-terminal amino acid and enable the synthesis of very pure peptides.

The incorporation of alpha-trifluoromethyl substituted amino acids into peptides increases proteolytic stability, enhances lipophilicity, and induces secondary structures. Read on to find out more!

Serine- and Threonine-derived oxazolidines as well as Cysteine-derived thiazolidines, so-called Pseudoprolines, serve as structure-disrupting, solubilizing building blocks in peptide synthesis.

Interested in studying the effect of palmitoylation on your peptide’s localization, function, and stability? Read on to find out more about the use of lipidated “fatty” amino acids!

Interested in structure activity studies on your Arginine containing peptide or further optimization for improved receptor binding? Explore our guanidino Proline derivatives as rigid Arginine mimics.

Are you using the Fmoc-MeDbz-OH Dawson Linker in large scale on a regular basis? A robust and economic processallows us to promptly provide you with kg quantities at competitive prices and in high quality.

Fmoc-Asp(CSY)-OH – an innovative building block to suppress aspartimide formation during peptide synthesis by utilizing cyanosulfurylide as carboxylic acid protecting group. Read on to find our more!

Herein, we present aminooxy-amino acids reported for peptide synthesis via oxime ligation, cyclization via oxime formation, derivatization e.g. by glycosylation, or chelation. Read on to find out more.

Herein we present two arginine derivatives, in which the native guanidino group is replaced by an isosteric amino-functionalized carbamoylated guanidino group that can serve as an attachment point for further derivatization.

Frustrated by aspartimide formation during peptide synthesis? Iris Biotech presents aspartate derivatives with bulky side chain protecting groups that minimize the formation of aspartimide-related side-products.

Interested in the formation of peptide thioesters for Native Chemical Ligation? Read on to find out more about the use of Dawson Linker derivatives as thioester surrogates compatible with Fmoc SPPS.

Enzymatically-activatable probes based on 7-amino-4-methylcoumarin (AMC) represent versatile tools for the detection and localization of proteolytic enzyme activities. Read on to find out more.

Methionine is particularly prone to oxidation by atmospheric oxygen in vitro but also by reactive oxygen species in vivo, resulting in the corresponding sulfoxide and sulfone. Read on to find out more.

Nitrodibenzofuran (NDBF) is a photocleavable side chain protecting group that can be removed by photolysis upon irradiation with UV-light or – especially for in vivo applications – by two-photon excitation using near infrared light.

Iris Biotech presents the next-generation of hydrolysis-stable phosphono-analogs of pSer, pThr and pTyr. Fluorination renders the phosphonic acid more acidic and thus an even better mimic of the parent phosphoamino acid.

Find out more about those building blocks with side chains able to coordinate metal ions, and why peptide-based HDACis are intriguing synthetic targets.

Placing Dde as one terminal group of a linker and a functional group prone for conjugation as the other or using Dde as the central connective portion of a linker, allows for the creation of new bifunctional linkers.

The Allocam protecting group allows for selective deprotection and disulfide bond formation on-resin in one step.

Two selected publications were summarized in this article in order to highlight the impressive utility of amino acids incorporating the diazirine photophore.

Phosphorylation of serine, threonine and tyrosine is counted among the most important posttranslational modifications that occur in organisms.

Iris Biotech introduces a comprehensive set of photo-crosslinking amino acids bearing the diazirine moiety.

The most common reagent for the Fmoc-protection of amino acids is currently Fmoc-OSu, followed by Fmoc-Cl. However, the use of these reagents is usually accompanied by several side reactions, such as the formation of beta-alanine and dipeptides.

The Fmoc group is the most frequently used protecting group in peptide chemistry. The most common deprotection conditions involve a solution of 20% piperidine in DMF.

Amino acids of high quality are crucial for the synthesis of peptides with a high purity.

As Boc and Fmoc protected derivatives of both azido and alkyne amino acids are available, they can be introduced into peptide sequences through standard SPPS protocols, for example. In an α-helical secondary structure amino acids at positions i and i+4 are above each other.

The azido group can be reduced to an amino function and hereby serve as masked amino group. It is of particular use if additional orthogonalities are needed. Azido is stable towards treatment with piperidine (Fmoc deprotection), Pd(0) (Alloc removal) and acidic treatmet (cleavage of Mtt, Trt or other acid sensitive groups). However, as it is a pseudohalogenide, care has to be taken during coupling steps, as HATU will cause high racemization. This can be avoided using collidine or other non-nucleophilic bas...

The incorporation of trifluoromethyl group carrying building blocks into peptides results in increased chemical and thermal stability, increased resistance to degradation by proteases, and enhanced lipophilicity.

Trypsin (EC 3.4.21.4), an endopeptidase and natural protease found in the digestive system, cleaves peptide chains and proteins predominantly at the carboxyl side of the amino acids Lys and Arg (except when followed by Pro).

Abstract: A symposium report. Protected peptides were synthesized using 9-fluorenylmethoxycarbonyl (Fmoc) amino acids and the acid labile 2-chlorotrityl and the multidetachable 2-chlorotrityl-Rink-linker resins.

Abstract: Ditrityl amino acids Trt-Lys(Trt)-OH (Trt = CPh3), Trt-Orn(Trt)-OH, Trt-Ser(Trt)-OH, and Trt-Hse(Trt)-OH were prepared and used in the synthesis of trityl-protected peptides, e.g., Trt-Ser(Trt)-Phe-NH2.

In this news section, we highlight three useful coupling reagents for peptide chemistry: PyCLOCK, PyAOP and HDMA.

Fmoc-L-Dap(2-Boc-aminoethyl)-OH is the first in a series of new triamino acid building blocks. This azalysine is useful for introducing positive charges into a peptide, or for creating branched structures.

This innovative auxiliary facilitates Native Chemical Ligation at the position of a Glycine residue in a peptide sequence. The auxiliary can be further functionalized, e.g. by PEGylation. Following NCL, the auxiliary is removed by irradiation with UV light.

The classic FRET pair EDANS and DABCYL is now available linked to Fmoc amino acid building blocks that can be readily used in SPPS. Conveniently synthesize your own custom protease substrates!

The SCAL linker offers superior chemical stability and permits a variety of orthogonal solid-phase approaches. It is fully compatible with the Fmoc-, Boc- and Alloc- strategies. Cleavage can be performed either by a simultaneous, or by a two-step reduction/acidolysis procedure to afford peptide amides.

Peptides as pharmaceutical compounds suffer from unfavorable pharmacokinetics which is, among other things, due to a slow uptake into cells and rapid proteolytic cleavage. N -Alkylation of peptides is a valuable tool to overcome these limitations. We now offer new kits that enable the facile preparation of peptoids and N -alkylated peptides.

The regioselective formation of multiple disulfide bonds is often a synthetic challenge. We now offer an innovative safety-catch Cys protecting group that allows selective deprotection of the sulfhydryl group and is a valuable addition to the peptide chemist’s toolbox.

2-Furyl-alanine can be incorporated into peptides via SPPS or by using enzymatic approaches. UV-irradiation in the presence of oxygen and a photosensitizer converts furyl-alanine to an intermediate that selectively reacts with certain nucleophiles. This property can be employed for site-specific labeling of peptides and proteins.

The Fmoc-L-Phe-Aca pseudo-dipeptide is a useful reporter group for the successful internalization of CPPs. Phe quenches the fluorescence of Aca. Internalization of the peptide containing Phe-Aca leads to proteolytic cleavage of the Phe-Aca bond and thus to fluorescence.

5-oxa-Derivatives of Orn and Arg, respectively, these rare amino acids are produced by legumes as protection against herbivores. For your convenience, we offer building blocks of both amino acids compatible with standard Fmoc/ t Bu SPPS chemistry

N δ -hydroxy- N δ -acetyl-ornithine, an important constituent of many siderophores, is now available for your convenience as  N α -Fmoc- N δ -(acetyl)- N δ -(benzoyloxy)-ornithine  building block which can be used in standard Fmoc/ t Bu SPPS and permits facile on-resin  N δ -deprotection.

Click chemistry is a convenient method to chemoselectively functionalize peptides at specific positions. We offer a variety of different propargyl amino acids for both Fmoc and Boc strategies, for enzymatic synthesis, as well as preloaded resins for SPPS.

Pre-packed amino acid cartridges for ABI peptide synthesizers are available for you convenience. Speed up your peptide syntheses with our cartridges containing all 20 standard amino acids for Fmoc/tBu chemistry.

Peptide linkers usually are cleaved under acidic conditions or using two-step procedures. Photocleavage proceeds under neutral conditions using UV light and can either be performed in batch or using flow chemistry.

Surprising behavior of NXO-peptides. It is a significant property of peptides that oxalo-retro azapeptides have the same donor and acceptor distances and properties for hydrogen bridge formation as a tripeptide fragment and therefore induce beta-sheet formation at this position.

A new hydrazone resin enables a convenient way to synthesize peptide hydrazides for Hydrazone Ligation Technique and Native Chemical Ligation (NCL).

A set of new statin analogues, so called Super-Threonines, is available consisting of Fmoc protected L-enantiomers with all possible 4 stereoisomers of chiral centers in the side chain. They appear in nature as bridge building element in cyclodepsipeptides, like pipecolidepsin A, a compound which shows relevant cytotoxic activity in three human tumor cell lines (lung, colon, breast) and has unique structural features.

Wang resins are widely used for peptide synthesis. However, certain side reactions, like diketopiperazin formation limit their use. 4-Methylbenzhydryl resin needs more space and leaves less room for this type of side reactions. Standard “Wang-typical” Fmoc/tBu coupling protocols can be applied.

Pseudoprolines derived from Serine and Threonine have developed to standard building blocks for peptide synthesis since their invention. Now this technology is also available with Cysteine residues, as the corresponding 2,4-dimethoxyphenyl-pseudothiaproline is compatible with standard Fmoc/tBu protocols.

Positions next to Glycine are often reasons for side reactions, as aspartamide or diketopiperazine formation can occur. Dmb and Tmb can be used for temporary protection of the amide nitrogen of a peptide bond, in order to solubilize the peptide and increase yield and purity.

Peptide hydrazides can be easily synthesized using a new hydrazone resin, obtained via acylation of aminomethyl polystyrene by Fmoc-hydrazone of pyruvic acid.

Fmoc-Sieber amide resin is an acid-labile carrier for solid phase synthesis of peptide amides. Cleavage with only 1% TFA makes it an ideal carrier for the synthesis of protected peptide fragments in fragment condensation strategies for the synthesis of long peptides.

alpha-Sulfo-beta-Alanine has been used to couple to hydrophobic molecules and peptides and increase solubility. Attachment can be carried out by conventional Fmoc/tBu protocols.

Used for Efficient and Economic Bulk Synthesis of Peptide APIs: A new technology is available with a set of new preloaded resins, which enable the synthesis of peptide amides WITHOUT ANY LINKER. Amino acid amides, which bear a functional side chain, are immobilized on acid sensitive resins. This makes process development, small scale synthesis, bulk production and in-process control very easy. Find more technical details in our application for demonstration purposes with BIVALIRUDIN.

Benzotriazol activated carboxylic acids: Fast reaction (within minutes) at room temperature with amines and other nucleophiles under addition of base (in both water and non- aqueous solvents). Stable to racemization when coupling with nucleophiles. High solubility in organic solvents like DMF and DCM. Stable in water.

Arginine rich peptides show increased interest during the last years as the have the capability to cross cell and blood brain barrier membranes.

Any amino acid can be functionalized on the N-terminus with oxalic acid and on the C-terminus with hydrazine, in order to form a so-called NXO building block. Through this double modification N and C terminus will be inverted, which provides interesting structural options for peptidomimetics.

The azido function can be used for different applications

Building Blocks for the synthesis of 2,3-diaminobutanoic acid containing peptides or for Click reactions.

Our portfolio currently contains over 5500 products. Many of them – in particular standard consumables for peptide synthesis – are being produced in bulk quantities.  Therefore we can keep our prices also for lab quantities at very competitive level. In case of need for bulk quantities please inquire: - All 20 Proteinogenic  Fmoc-protected Amino Acids  are available in 100+ kg Lots;

alpha-Sulfo-beta-Alanine has been used to couple to hydrophobic labels like Cyanine and Rhodamine dyes and other hydrophobic residues to increase their solubility in water. As di- or tripeptide a further increase of hydrophilicity can be achieved. Fmoc-beta-Ala(SO3H)-OH can be coupled in SPPS by standard phosphonium or uronium based coupling reagents. In high throughput technologies for DNA sequencing and genomics charge-modified dye-labeled dideoxynucleoside-5’-triphosphates were synthesized for &ls...

H-L-Aha-OH*HCl H-L-Dab(N3)-OH 4-Azido-L-homoalanine (S)-2-Amino-4-azidobutanoic acid hydrochloride Formula:                    C 4 H 8 N 4 O 2 *HCl Molecular Weight:     144,13*35,45 g/mole CAS:  942518-29-8 CODE:  HAA5730 1g:       EUR    200,-    US$    300,-  5g:   ...

Reported applications: Introduction of 9-fluorenylmethyloxycarbonyl, trichloroethoxycarbonyl, and benzyloxycarbonyl amine protecting groups into O-unprotected hydroxylamino acids using succinimidyl carbonates; Anelka Paquet; Can. J. Chem. ; 1982; 60: 976. Widely Applicable Deprotection Method of 2,2,2-Trichloroethoxycarbonyl (Troc) Group Using Tetrabutylammonium Fluoride; Cheng-yuan Huanga; Ning Wanga; Katsumasa Fujikia; Yuji Otsukaa; Masao Akamatsua; Yukari Fujimotoa; Koichi Fukasea; Journal o...

PGA (Penicillin G Amidase, Penicillin Acylase, Penicillin Amidohydrolase from E.coli on acrylic resin, Systematic name: Penicillin amidohydrolase, E.C. 3.5.1.11) has an active pocket, which is very specific for phenyl acetic acid. The prominent commercial use is hydrolysis of a phenylacetamid bond during production of the penicillin API 6-APA (De Martin et al., J. Mol. Catal. B:Enzymatic 1999; 6: 437). The high specifity of PGA towards the Phenylacetyl moiety makes the use of Phacm as new alternative ...

A novel, ethylene glycol-based protecting group is designed and synthesized for use in solid phase peptide synthesis.

Abstract: N alpha-9-Fluorenylmethoxycarbonyl-N epsilon-4=methyltrityl-lysine, [Fmoc-Lys(Mtt)-OH], was prepared in two steps from lysine, in 42% overall yield.