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A stereocontrolled construction of 2-azido-2-deoxy-1,2-cis-α-galactosidic linkages utilizing 2-azido-4,6-O-benzylidene-2-deoxygalactopyranosyl diphenyl phosphates: stereoselective synthesis of mucin core 5 and core 7 structures
| Title: | A stereocontrolled construction of 2-azido-2-deoxy-1,2-cis-α-galactosidic linkages utilizing 2-azido-4,6-O-benzylidene-2-deoxygalactopyranosyl diphenyl phosphates: stereoselective synthesis of mucin core 5 and core 7 structures |
| Authors: | Kakita, Kosuke Browse this author | | Tsuda, Toshifumi Browse this author | | Suzuki, Noritoshi Browse this author | | Nakamura, Seiichi Browse this author | | Nambu, Hisanori Browse this author →KAKEN DB | | Hashimoto, Shunichi Browse this author →KAKEN DB |
| Keywords: | Carbohydrates | | Glycosylation | | TN-antigen | | Mucin | | Phosphates |
| Issue Date: | 24-Jun-2012 |
| Publisher: | Elsevier |
| Journal Title: | Tetrahedron |
| Volume: | 68 |
| Issue: | 25 |
| Start Page: | 5005 |
| End Page: | 5017 |
| Publisher DOI: | 10.1016/j.tet.2012.04.059 |
| Abstract: | TMSOTf-promoted glycosidation of 2-azido-4,6-O-benzylidene-2-deoxygalactosyl diphenyl phosphates with fluorenylmethoxycarbonyl (Fmoc)-protected serine and threonine derivatives in THF/Et2O (1:1) gave glycosyl amino acids in high yields and with excellent levels of α-selectivity (α/β=94:6-95:5). The synthetic utility of the present glycosidation method was demonstrated by a stereoselective synthesis of mucin-type glycopeptide core 5 and core 7 building blocks, which are suitable for Fmoc-based solid-phase synthesis of O-glycopeptides. |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/49671 |
| Appears in Collections: | 薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 南部 寿則
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