2007年3月
Synthesis of biantennary LacNAc-linked O-glycan (core 4) and glycopeptide thioester by benzyl protection strategy: rapid zinc reduction of GlcNTCA to GlcNAc by microwave irradiation
TETRAHEDRON
- ,
- ,
- ,
- 巻
- 63
- 号
- 10
- 開始ページ
- 2170
- 終了ページ
- 2181
- 記述言語
- 英語
- 掲載種別
- DOI
- 10.1016/j.tet.2006.12.088
- 出版者・発行元
- PERGAMON-ELSEVIER SCIENCE LTD
A synthetic method for the core 4 O-glycan-linked Ser and Thr was developed. Highly stereoselective 3-O- and 6-O-glycosylation was achieved by using two distinctively protected N-trichloroacetyllactosaminyl fluorides (3 and 12). Microwave-assisted Zn reduction rapidly and efficiently converted N-trichloroacetylglucosamine (GlcNTCA) to N-acetylglucosamine (GlcNAc). In order to demonstrate the usefulness of the protected core 4 O-glycan a segment (Gly(34)-Gly(58)) of emmprin (extracellular matrix metalloproteinase inducer), a cancer metastasis-related glycoprotein, was synthesized by the solid-phase method, utilizing the pentasaccharyl Thr (2) to introduce an O-glycan in place of the native N-glycan at Asn(44). (c) 2007 Elsevier Ltd. All rights reserved.
- リンク情報
- ID情報
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- DOI : 10.1016/j.tet.2006.12.088
- ISSN : 0040-4020
- CiNii Articles ID : 80018653144
- Web of Science ID : WOS:000244536500008