Synthesis of analogues of 3-deoxy- d- manno-octulosonic acid (KDO) as potential inhibitors of CMP-KDO synthetase

A series of derivatives of the 2-deoxy analogue of β-KDO (2,6-anhydro-3-deoxy- d- glycero- d- talo-octonic acid; ammonium salt, 2) has been synthesised as potential inhibitors of CMP-KDO synthetase, starting from methyl 2,6-anhydro-3-deoxy-4,5:7,8-di- O-isopropylidene- d- glycero- d- talo-octonate a...

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Bibliographic Details
Published in:Carbohydrate research 1987-09, Vol.166 (2), p.233-251
Main Authors: Luthman, Kristina, Claesson, Alf, Jansson, Anita M., Pring, Brian G.
Format: Article
Language:English
Subjects:
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Exact sciences and technology
Indicators and Reagents
Nucleotidyltransferases - antagonists & inhibitors
Organic chemistry
Preparations and properties
Structure-Activity Relationship
Sugar Acids - chemical synthesis
Sugar Acids - pharmacology
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Summary:A series of derivatives of the 2-deoxy analogue of β-KDO (2,6-anhydro-3-deoxy- d- glycero- d- talo-octonic acid; ammonium salt, 2) has been synthesised as potential inhibitors of CMP-KDO synthetase, starting from methyl 2,6-anhydro-3-deoxy-4,5:7,8-di- O-isopropylidene- d- glycero- d- talo-octonate and replacing the CO 2e group attached to C-2 variously by CONH 2, CONHOH, CH 2OH, CH 2PO(OH)(O −NH 3 +), COCH 2PO(OH) ▪, CH 2CO 2 −NH 4 +, CON-HCH 2CO 2 −NH 4 +, CONHBn, CONHHexyl, CO 2Bn, and CO 2Hexyl. Of these derivatives, the hydroxamic acid (CONHOH) was the best inhibitor of CMP-KDO synthetase, but was less potent than 2.
ISSN:0008-6215
1873-426X
DOI:10.1016/0008-6215(87)80060-5