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Peptide Structure Stabilization by Click Chemistry

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.

Azido-Masked Amino Function

Carbohydrates for Click Chemistry

Protein and lipid glycosilation is a life-governing and omnipresent process. Glycoconjugates display a multitude of biological effects from protein folding and stabilization, energy storage, cell surface interaction through molecular recognition motifs for cell-cell communication, and structural support and protection.

Click Chemistry in DNA Synthesis

Click Chemistry in DNA Synthesis - Applications and Procedures in DNA Synthesis

Standard approaches

Diethyl-acetamidomalonate Route: The probably most widely used first approach to unnatural amino acids goes via alkylation of diethyl acetamidomalonate.

Specific platforms

Asymmetric Phase-Transfer Reaction Phase-transfer alkylations e.g. with the chiral Maruoka catalyst result in unique α-mono substituted and α,α-disubstituted unnatural amino acids.

Homologization of natural amino acids

Several platforms are available to display the whole assortment of homo-amino acids, as well as the higher homologues β2-, β3-, their double substituted derivatives β2,2,2-, β3,3-, and corresponding γ-amino acids.

α-Methyl and β,β-dimethyl amino acids

α-Methyl and alkyl-amino acids can be produced by a number of platforms, where the (2S,4S)-4-methyl-2-phenyloxazolidin-5-one scaffold is one of the most popular one.

Trifluoromethylated and other Fluoro-amino acids

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.

Arginine Analogues

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).