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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
- Molecular weight:367.40 g/mol
- Purity :min. 98%
- Enantiomeric Purity:min. 99,7%
from $156.25
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/ja962780.
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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