Fmoc-L-Ser[Psi(Me,Me)Pro]-OH

Chemical name: (S)-3-(N-alpha-(9-Fluorenylmethyloxycarbonyl)-2,2-dimethyloxyzolidine-4-carboxylic acid // Synonyms: (S)-3-(((9H-fluoren-9-yl)methoxy)carbonyl)-2,2-dimethyloxazolidine-4-carboxylic acid, Fmoc-Ser[Psi(Me,Me)Pro]-OH

  • Product code:FAA8590
  • CAS No.:1201651-31-1
  • Formula:C21H21NO5
  • Storage temperature:2-8°C
  • Molecular weight:367.40 g/mol
  • Purity :min. 98%
  • Enantiomeric Purity:min. 99.7%

from $156.25

Grouped product items
Qty Packing unit Price SKU Availability
5 g
$156.25
FAA8590.0005
<10 business days
25 g
$625.00
FAA8590.0025
<10 business days
100 g
$1,875.00
FAA8590.0100
<10 business days
Safety Data Sheets
description

This building block is a pseudoproline monomer for SPPS. It can be successfully coupled with various amino acids using modern coupling techniques avoiding the need for pseudoproline dipeptides and giving the possibility to introduce pseudoprolines in peptides containing non-natural or rare amino acids. For coupling efficiency studies please see Senko et al, 2021.


references

Scope and limitations of pseudoprolines as individual amino acids in peptide synthesis; D. A. Senko, N. D. Timofeev, I. E. Kasheverov, I. A. Ivanov; Amino Acids 2021; 53: 665-671. https://doi.org/10.1007/s00726-021-02973-1


Pseudo-Prolines as a Molecular Hinge:  Reversible Induction of cis Amide Bonds into Peptide Backbones; P. Dumy, M. Keller, D. E. Ryan, B. Rohwedder, T. Wöhr and M. Mutter; J. Am. Chem. Soc. 1997; 119: 918-925. https://doi.org/10.1021/ja962780a

Pseudo-Prolines as a Solubilizing, Structure-Disrupting Protection Technique in Peptide Synthesis; T. Wöhr, F. Wahl, A. Nefzi, B. Rohwedder, T. Sato, X. Sun and M. Mutter; J. Am. Chem. Soc. 1996; 118: 9218-9227. https://doi.org/10.1021/ja961509q


Expediting the Fmoc solid phase synthesis of long peptides through the application of dimethyloxazolidine dipeptides; P. White, J. W. Keyte, K. Bailey and G. Bloomberg; J. Pept. Sci. 2004; 10: 18-26. https://doi.org/10.1002/psc.484


Pseudoprolines as Removable Turn Inducers: Tools for the Cyclization of Small Peptides; D. Skropeta, K. A. Jolliffe, and P. Turner; J. Org. Chem. 2004; 69: 8804-8809. https://doi.org/10.1021/jo0484732

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