Synthesis of Core-class 2O-Linked Glycopeptides: a Benzyl-protected Tetrasaccharyl Serine and its Derivative Carrying a Hydrophobic Cholestanyl Group | Zendy

Jun Watabe | Zendy; Latika Singh | Zendy; Yuko Nakahara | Zendy; Yukishige Ito | Zendy; Hironobu Hojo | Zendy; Yoshiaki Nakahara | Zendy

Open Access

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

Author(s) -

Jun Watabe,

Latika Singh,

Yuko Nakahara,

Yukishige Ito,

Hironobu Hojo,

Yoshiaki Nakahara

Publication year - 2002

Publication title -

bioscience biotechnology and biochemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.509

H-Index - 116

eISSN - 1347-6947

pISSN - 0916-8451

DOI - 10.1271/bbb.66.1904

Subject(s) - tetrasaccharide , chemistry , serine , glycosyl donor , glycosylation , stereochemistry , glycosyl , protecting group , disaccharide , glycopeptide , conjugate , organic chemistry , biochemistry , polysaccharide , mathematical analysis , alkyl , mathematics , enzyme , antibiotics

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 alpha- and beta-glycosides in 40% and 33% yields, respectively. Alpha-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.

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