Stereoselective total synthesis of acremomannolipin A and its anomer,the potent calcium signal modulators with a novel glycolipid structure: role of the stereochemistry at the anomeric center on the activity |
| |
| Authors: | Nozomi Tsutsui Genzoh Tanabe Genki Gotoh Ayako Kita Reiko Sugiura Osamu Muraoka |
| |
| Institution: | 1. Laboratory of Pharmaceutical Organic Chemistry, School of Pharmacy, Kinki University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan;2. Laboratory of Molecular Pharmacogenomics, School of Pharmacy, Kinki University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan |
| |
| Abstract: | A full account of stereoselective total synthesis of a novel glycolipid, acremomannolipin A (1), the potent calcium signal modulator isolated from Acremonium strictum, by employing the stereoselective β-mannosylation of 4,6-O-benzylidene-protected mannosyl sulfoxide with d-mannitol as the key reaction is described. The α-anomer (epi-1) of 1 was also synthesized selectively. The calcium modulating activity was reduced upon inversion of the configuration at the anomeric center, indicating that the β-configuration of the mannose moiety is preferable for the activity. |
| |
| Keywords: | Acremomannolipin A Glycolipid Calcium signal modulator Selective β-mannosylation Acremonium strictum |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
