Synthesis of Core-class 2 O-Linked Glycopeptides : a Benzyl-protected Tetrasaccharyl Serine and its Derivative Carrying a Hydrophobic Cholestanyl Group(Organic Chemistry)

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概要

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• A core-class 2 tetrasaccharide-linked serine was synthesized in a convergent manner. The coupling reaction of disaccharide glycosyl donor 3 and acceptor 4 stereoselectively afforded tetrasaccharide 15, which was converted to glycosyl fluoride 20. Glycosylation of Fmoc serine allyl ester 5 with 20 produced α- and β-glycosides in 40% and 33% yields, respectively, α-Isomer 21 was converted into 1, a useful building block for the solid-phase synthesis of glycopeptides. On the other hand, 21 was N-deprotected and condensed with hydrophobic cholestanol through a succinyl spacer. The same compound was alternatively synthesized by coupling 20 and 28. Functional group manipulation and hydrogenation afforded core 2 tetrasaccharide-cholestanol conjugate 2.

• 社団法人日本農芸化学会の論文
• 2002-09-23

著者

• Ito Yukishige

  The Institute Of Physical And Chemical Research (riken)

• HOJO Hironobu

  Institute for Protein Research, Osaka University

• NAKAHARA Yuko

  The Institute of Physical and Chemical Research (RIKEN)

• Watabe Jun

  Institute Of Glycotechnology Department Of Applied Biochemistry Tokai University

• SINGH Latika

  The Institute of Physical and Chemical Research (RIKEN)

• NAKAHARA Yoshiaki

  Institute of Glycotechnology, Department of Applied Biochemistry, Tokai University

• Hojo Hironobu

  Institute For Protein Research Osaka University

• Singh Latika

  The Institute Of Physical And Chemical Research (riken):crest Japan Science And Technology Corporati

• Ito Yukishige

  Riken Advanced Science Institute

• Nakahara Y

  Department Of Applied Biochemistry Institute Of Glycoscience Tokai University

• Hojo H

  Department Of Applied Biochemistry Institute Of Glycoscience Tokai University

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