Synthesis of enantiomerically enriched (R)-13C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine-Reference-Cited by-同舟云学术

Synthesis of enantiomerically enriched (R)-13C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine

Published:2011-09-20 Issue: Volume:7 Page:1304-1309
ISSN:1860-5397
Container-title:Beilstein Journal of Organic Chemistry
language:en
Short-container-title:Beilstein J. Org. Chem.

Author:

Fletcher Stephen P,Solà Jordi,Holt Dean,Brown Robert A,Clayden Jonathan

Abstract

The method of Kouklovsky and coworkers for the enantioselective alkylation of cyclic N-naphthoyl derivatives of amino acids was used to introduce a 13C label into one of the two enantiotopic methyl groups of 2-aminoisobutyric acid (Aib) by retentive alkylation of L-alanine with 13CH3I. Conditions were identified for optimization of yield and enantiomeric purity, and the absolute configuration of the labelled product was established.

Publisher

Beilstein Institut

Subject

Organic Chemistry

Link

https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-7-152.pdf

Reference57 articles.

1. A Field Guide to Foldamers

2. Aromatic δ-peptides: design, synthesis and structural studies of helical, quinoline-derived oligoamide foldamers

3. Dynamic Helical Structures: Detection and Amplification of Chirality

4. Quantifying End-to-End Conformational Communication of Chirality through an Achiral Peptide Chain

5. N- versus C-Terminal Control over the Screw-Sense Preference of the Configurationally Achiral, Conformationally Helical Peptide Motif Aib8GlyAib8

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