An easy α-glycosylation methodology for the synthesis and stereochemistry of mycoplasma α-glycolipid antigens.

Beilstein Journal of Organic Chemistry
Yoshihiro NishidaKazuhiro Matsuda

Abstract

Mycoplasma fermentans possesses unique α-glycolipid antigens (GGPL-I and GGPL-III) at the cytoplasm membrane, which carry a phosphocholine group at the sugar primary (6-OH) position. This paper describes a practical synthetic pathway to a GGPL-I homologue (C(16:0)) and its diastereomer, in which our one-pot α-glycosylation method was effectively applied. The synthetic GGPL-I isomers were characterized with (1)H NMR spectroscopy to determine the equilibrium among the three conformers (gg, gt, tg) at the acyclic glycerol moiety. The natural GGPL-I isomer was found to prefer gt (54%) and gg (39%) conformers around the lipid tail, while adopting all of the three conformers with equal probability around the sugar position. This property was very close to what we have observed with respect to the conformation of phosphatidylcholine (DPPC), suggesting that the Mycoplasma glycolipids GGPLs may constitute the cytoplasm fluid membrane together with ubiquitous phospholipids, without inducing stereochemical stress.

References

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Oct 23, 1997·The Journal of Biological Chemistry·U ZähringerS Rottem
Oct 6, 2000·Microbiology and Immunology·K MatsudaN Yamamoto
Jul 5, 2003·Organic Letters·Yoshihiro NishidaKazukiyo Kobayashi
Jul 19, 2003·European Journal of Biochemistry·Klaus BrandenburgUlrich Seydel
Apr 2, 2004·Current Microbiology·Francisco RomeroMaría Jiménez-Valera
Aug 24, 2004·Infection and Immunity·Amichai YavlovichShlomo Rottem
Mar 1, 2008·Biochemical and Biophysical Research Communications·Yutaka KawahitoKazuhiro Matsuda
Feb 6, 2010·The Journal of Veterinary Medical Science·Masatoshi FujiharaRyô Harasawa
Mar 17, 2010·Journal of Bioscience and Bioengineering·Noriko IshidaKozo Asano

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Citations

Nov 5, 2013·Organic Letters·Sebastian Schmalisch, Rainer Mahrwald
Aug 21, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Natarajan ArumugamHasnah Osman
Nov 11, 2014·Beilstein Journal of Organic Chemistry·Thisbe K Lindhorst

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Methods Mentioned

BETA
NMR
glycosylation
column
silica
silica gel column chromatography
column chromatography

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