A concise synthesis of the O-glycosylated amino acid building block; using phenyl selenoglycoside as a glycosyl donor

Weir Torn Jiaang; Meng Yang Chang; Ping Hui Tseng; Shui Tein Chen

doi:10.1016/S0040-4039(00)00367-1

A concise synthesis of the O-glycosylated amino acid building block; using phenyl selenoglycoside as a glycosyl donor

Weir Torn Jiaang, Meng Yang Chang, Ping Hui Tseng, Shui Tein Chen

Institute of Biochemistry and Molecular Biology

Research output: Contribution to journal › Article › peer-review

50 Scopus citations

Abstract

A new glycosylation methodology for synthesizing a protected TF antigen is described. The key step is to use phenyl selenoglycoside as a glycosyl donor, thereby successfully establishing O-linked Fmoc-protected threoninyl monosaccharide in an excellent yield with high α selectivity. From protected D-galactal, a protected TF antigen building block is obtained in 40% total yield.

Original language	English
Pages (from-to)	3127-3130
Number of pages	4
Journal	Tetrahedron Letters
Volume	41
Issue number	17
DOIs	https://doi.org/10.1016/S0040-4039(00)00367-1
State	Published - 22 Apr 2000

Keywords

Building block
Phenyl selenoglycoside
TF antigen
Tetramethylurea

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10.1016/S0040-4039(00)00367-1

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title = "A concise synthesis of the O-glycosylated amino acid building block; using phenyl selenoglycoside as a glycosyl donor",

abstract = "A new glycosylation methodology for synthesizing a protected TF antigen is described. The key step is to use phenyl selenoglycoside as a glycosyl donor, thereby successfully establishing O-linked Fmoc-protected threoninyl monosaccharide in an excellent yield with high α selectivity. From protected D-galactal, a protected TF antigen building block is obtained in 40% total yield.",

keywords = "Building block, Phenyl selenoglycoside, TF antigen, Tetramethylurea",

author = "Jiaang, {Weir Torn} and Chang, {Meng Yang} and Tseng, {Ping Hui} and Chen, {Shui Tein}",

note = "Funding Information: Support for this research provided by the National Science Council, Taiwan, is gratefully acknowledged.",

year = "2000",

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doi = "10.1016/S0040-4039(00)00367-1",

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T1 - A concise synthesis of the O-glycosylated amino acid building block; using phenyl selenoglycoside as a glycosyl donor

AU - Jiaang, Weir Torn

AU - Chang, Meng Yang

AU - Tseng, Ping Hui

AU - Chen, Shui Tein

N1 - Funding Information: Support for this research provided by the National Science Council, Taiwan, is gratefully acknowledged.

PY - 2000/4/22

Y1 - 2000/4/22

N2 - A new glycosylation methodology for synthesizing a protected TF antigen is described. The key step is to use phenyl selenoglycoside as a glycosyl donor, thereby successfully establishing O-linked Fmoc-protected threoninyl monosaccharide in an excellent yield with high α selectivity. From protected D-galactal, a protected TF antigen building block is obtained in 40% total yield.

AB - A new glycosylation methodology for synthesizing a protected TF antigen is described. The key step is to use phenyl selenoglycoside as a glycosyl donor, thereby successfully establishing O-linked Fmoc-protected threoninyl monosaccharide in an excellent yield with high α selectivity. From protected D-galactal, a protected TF antigen building block is obtained in 40% total yield.

KW - Building block

KW - Phenyl selenoglycoside

KW - TF antigen

KW - Tetramethylurea

UR - http://www.scopus.com/inward/record.url?scp=0034701517&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)00367-1

DO - 10.1016/S0040-4039(00)00367-1

M3 - Article

AN - SCOPUS:0034701517

SN - 0040-4039

VL - 41

SP - 3127

EP - 3130

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 17

ER -

A concise synthesis of the O-glycosylated amino acid building block; using phenyl selenoglycoside as a glycosyl donor

Abstract

Keywords

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