Synthesis of a natural oligosaccharide antibiotic active against Helicobacter pylori.
An oligosaccharide active against Helicobacter pylori was synthesized in a highly efficient manner for the first time. The anti-H. pylori oligosaccharide structure is a core-2 branched-type oligosaccharide with a characteristic alpha-N-acetylglucosamine at the nonreducing end. The oligosaccharide was synthesized from the nonreducing end to the reducing end, with an N-benzyl-2,3-oxazolidinone-carrying glycosyl donor used to introduce an alpha-N-acetylglucosamine at the nonreducing end. Complete chemoselective activation of a bromo sugar in the presence of a thioglycoside acceptor was achieved, and the use of 2,6-dimethylphenyl thioglycoside prevented the aglycon transfer observed when the corresponding phenyl thioglycoside is used as an acceptor.
Manabe
Shino
S
RIKEN (The Institute of Physical and Chemical Research), 2-1 Hirosawa, Wako, Saitama 351-0198, Japan. smanabe@riken.jp
Ishii
Kazuyuki
K
Ito
Yukishige
Y
D000117:Acetylglucosamine / Q000737:chemistry; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry; D002626:Chemistry, Pharmaceutical / Q000379:methods; D015195:Drug Design; D006031:Glycosylation; D016480:Helicobacter pylori / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009844:Oligosaccharides / Q000737:chemistry / Q000494:pharmacology*; D010587:Phagocytosis; D013865:Thioglycosides / Q000737:chemistry
D000890:Anti-Infective Agents; D002241:Carbohydrates; D009844:Oligosaccharides; D013865:Thioglycosides; D000117:Acetylglucosamine