Jul, 2015
Structure-activity relationship studies on acremomannolipin A, the potent calcium signal modulator with a novel glycolipid structure 3: Role of the length of alditol side chain
BIOORGANIC & MEDICINAL CHEMISTRY
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- Volume
- 23
- Number
- 13
- First page
- 3761
- Last page
- 3773
- Language
- English
- Publishing type
- Research paper (scientific journal)
- DOI
- 10.1016/j.bmc.2015.03.079
- Publisher
- PERGAMON-ELSEVIER SCIENCE LTD
Five homologs of a novel glycolipid acremomannolipin A (1a), the potential Ca2+ signal modulator isolated from Acremonium strictum, bearing alditols of different length (1g-1k) were synthesized by a stereoselective beta-mannosylation of appropriately protected mannosyl sulfoxide (2) with five alditols (1g: C2, 1h: C3, 1i: C4, 1j: C5 and 1k: C7 units), and their potential in modulating Ca2+ signaling were evaluated. Homologs with alditols of more than 4 carbons (1i, 1j and 1k) were equally or more potent than the parent compound (1a) regardless of the length of the alditol chain. Whereas activities of two homologs with shorter chains (1g and 1h) decreased to a considerable extent. The results indicated that the length of the alditol side chain was a crucial determinant for the potent calcium signal modulating activity. (C) 2015 Elsevier Ltd. All rights reserved.
- Link information
- ID information
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- DOI : 10.1016/j.bmc.2015.03.079
- ISSN : 0968-0896
- eISSN : 1464-3391
- Pubmed ID : 25910586
- Web of Science ID : WOS:000355848900082