Synthesis of Novel Tetrahydropyran-Based Dipeptide Isosters by Overman Rearrangement of 2,3-Didehydroglycosides

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 nat...

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Bibliographic Details
Published in:European journal of organic chemistry 2003-07, Vol.2003 (13), p.2418-2427
Main Authors: 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.
Format: Article
Language:English
Subjects:
Antigenic peptide
Dipeptide isosters
Overman rearrangement
Solid-phase peptide synthesis
Sugar amino acids
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Summary: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)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200200710