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Stereocontrolled synthesis of peptide bond isosteres
Author(s) -
Whitesell James K.,
Lawrence Robert M.
Publication year - 1989
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530010116
Subject(s) - chemistry , peptide , peptide bond , combinatorial chemistry , stereochemistry , biochemistry
Absolute stereochemical control is employed in the synthesis of isosteres for dipeptide subunits 1; see Fig. (1) in which the amide linkage has been replaced by a trans carbon‐caron double bond. The synthesis affords access to the four stereoisomers of 1 in which R and R' = CH 3 , including the isostere of D‐alanine‐d‐alanine (D‐ala‐D‐Ala), 2.