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Synthesis of Conformationally Restricted Mimetics of γ ‐Turns and Incorporation into Desmopressin, an Analogue of the Peptide Hormone Vasopressin
Author(s) -
Brickmann Kay,
Yuan ZhongQing,
Sethson Ingmar,
Somfai Peter,
Kihlberg Jan
Publication year - 1999
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(19990802)5:8<2241::aid-chem2241>3.0.co;2-l
Subject(s) - peptidomimetic , peptide , desmopressin , vasopressin , enantioselective synthesis , combinatorial chemistry , chemistry , stereochemistry , biochemistry , medicine , endocrinology , catalysis
Peptide secondary structure mimetics should accurately imitate the desired backbone conformation, and synthetic routes to peptidomimetics should allow for flexible introduction of side chains with correct stereochemistry. Both criteria are met by the enantioselective approach presented here. Mimetics of inverse and classical γ ‐turns ( 1 and 2 , respectively) were assembled from three types of building blocks, all of which can be prepared in a few steps from commercially available starting materials.