Premium
Synthesis of β‐(1→2)‐Linked Oligomannosides
Author(s) -
Poláková Monika,
Roslund Mattias U.,
Ekholm Filip S.,
Saloranta Tiina,
Leino Reko
Publication year - 2009
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.200801024
Subject(s) - chemistry , candida albicans , stereoselectivity , combinatorial chemistry , stereochemistry , total synthesis , oligosaccharide , antifungal , computational biology , biochemistry , microbiology and biotechnology , biology , catalysis
β‐(1→2)‐Linked oligomannosides constitute an important class of carbohydrate structures located on the cell surface of several Candida species, including C. albicans . As a result of the immunostimulating properties of such compounds, the upscaling of their synthesis is relevant. In this paper, a highly stereoselective synthesis of β‐(1→2)‐linked oligomannosides was performed by further development of and modifications to the methodologies described earlier in the literature. In addition to the synthesis of fully deprotected β‐(1→2)‐linked mannobiose and mannotriose, some preliminary modifications to the oligosaccharide core, resulting in close analogues with biological potential, are presented. The fully deprotected products form potential targets for screening against C. albicans and may also result in new model structures for vaccine development.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)