CATALYSE INTRAMOLECULAIRE DE L'AMINOLYSE DES HETEROCYCLES PHOSPHORES DERIVES DES α AMINOAMIDES. II: ETUDE DE LA CYCLISATION DES PHOSPHORDIAMIDES INCORPORANT UN RESIDU DE β AMINOACIDE, REACTIVITE VIS A VIS DE NUCLEOPHILES DES HETEROCYCLES FORMES

Derivatives of β aminoacids in form of esters 1 or nitrile 4 (table I) undergo in an alcohol-ate/alcohol medium a rearrangement (Fig. 2), with formation of a β peptide link, resulting in the formation of esters 6 (table II). According to the experimental conditions the six membered ring heterocycles...

Full description

Saved in:
Bibliographic Details
Published in:Phosphorus, sulfur, and silicon and the related elements sulfur, and silicon and the related elements, 2000-02, Vol.157 (1), p.165-191
Main Authors: Dujols, Frederic, Mulliez, Michel
Format: Article
Language:English
Subjects:
cyclization
intramolecular catalysis
Peptide synthesis
phosphorylation
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Derivatives of β aminoacids in form of esters 1 or nitrile 4 (table I) undergo in an alcohol-ate/alcohol medium a rearrangement (Fig. 2), with formation of a β peptide link, resulting in the formation of esters 6 (table II). According to the experimental conditions the six membered ring heterocycles 5 are detected or isolated. They are also synthetized by cyclisation of acids 2 or hydrazide 3 (Fig. 5). While phosphorus easily reacts with alcohols and water, leading respectively to esters 6 and acids 9 (Fig. 7), it remains unaffected by amines. These results are discussed in term of mechanisms of the phosphorylation. The applications for β peptide synthesis and the participation of the p amide group in phosphorylation are limited.
ISSN:1042-6507
1563-5325
DOI:10.1080/10426500008040521