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Application of Reductive Samariation to the Synthesis of Small Unnatural Peptides
Author(s) -
Ricci Marina,
Madariaga Leire,
Skrydstrup Troels
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(20000103)39:1<242::aid-anie242>3.0.co;2-r
Subject(s) - tripeptide , amide , yield (engineering) , chemistry , deprotonation , peptide bond , dipeptide , combinatorial chemistry , substrate (aquarium) , reductive elimination , stereochemistry , organic chemistry , peptide , catalysis , materials science , biochemistry , ion , oceanography , metallurgy , enzyme , geology
Considering that the amide NH groups are neither protected nor deprotonated , reductive samariation in the presence of a carbonyl substrate is a remarkably efficient method for the formation of a C−C bond. This was shown for a series of dipeptides and a tripeptide [Eq. (a)]. For the latter the product was obtained in a good yield of 50 %, despite the presence of three amide protons.