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Synthesis of Novel Tetrahydropyran‐Based Dipeptide Isosters by Overman Rearrangement of 2,3‐Didehydroglycosides
Author(s) -
Kriek Nicole M. A. J.,
Hout Elise van der,
Kelly Paskal,
Meijgaarden Krista E. van,
Geluk Annemieke,
Ottenhoff Tom H. M.,
Marel Gijs A. van der,
Overhand Mark,
Boom Jacques H. van,
Valentijn A. Rob P. M.,
Overkleeft Herman S.
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200200710
Subject(s) - dipeptide , chemistry , tetrahydropyran , moiety , stereochemistry , mycobacterium tuberculosis , peptide , combinatorial chemistry , organic chemistry , biochemistry , tuberculosis , ring (chemistry) , medicine , pathology
Differently functionalized tetrahydropyran‐based dipeptide isosters have been efficiently synthesized from 3,4,6‐tri‐ O ‐acetyl‐ D ‐glucal. Analogues of the hsp65 p2−13 epitope of Mycobacterium tuberculosis and Mycobacterium leprae were prepared by replacement of the Ala−Tyr or Glu−Glu moiety in the native dodecapeptide with the prepared dipeptide isosters. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)