Synthesis of carbocyclic analogues of the mannosyl trisaccharide: ether- and imino-linked methyl 3,6-bis(5a-carba-alpha-D-mannopyranosyl)-3,6-dideoxy-alpha-D-mannopyran osides.
Carbocyclic analogues 2 and 3 of the "trimannosyl structure 1", methyl 3,6-bis(5a-carba-alpha-D-mannopyranosyl)-3,6-dideoxy-alpha-D-ma nnopyranosides bonded by way of respective ether and imino linkages, were synthesized. The ether 2 had no inhibitory activity against alpha-D-mannosidase; in contrast, the imino compound 3 was a mild inhibitor. Furthermore, the inhibitory activity of 4, related to 3 by introduction of unsaturation between C-5 and C-5a of the carba-sugar moieties, was shown to be somewhat greater.
Ogawa
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S
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Yokohama, Japan.
Sasaki
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S
Tsunoda
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H
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004987:Ethers / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008358:Mannose / Q000737:chemistry* / Q000378:metabolism; D008361:Mannosidases / Q000037:antagonists & inhibitors / Q000378:metabolism; D008362:Mannosides / Q000138:chemical synthesis* / Q000494:pharmacology; D008969:Molecular Sequence Data; D015394:Molecular Structure; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000494:pharmacology; D043323:alpha-Mannosidase
D004987:Ethers; D008362:Mannosides; D014312:Trisaccharides; D008361:Mannosidases; D043323:alpha-Mannosidase; D008358:Mannose