D-galactofuranosylphosphonates.: First synthesis of UDP-C-D-galactofuranose

被引：44

作者：

Kovensky, J

McNeil, M

Sinay, P

机构：

[1] Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Quim Organ, RA-1428 Buenos Aires, DF, Argentina

[2] Colorado State Univ, Dept Microbiol, Ft Collins, CO 80523 USA

[3] Ecole Normale Super, Dept Chim, URA 1686, F-75231 Paris, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 17期

关键词：

D O I：

10.1021/jo990196p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chemical synthesis of two phosphono analogues of D-galactofuranosyl phosphate was performed. The natural phosphate seemed to be too labile to allow the chemical synthesis of UDP-Galf, these C-galactofuranosides are stable pharmacophores, and the cr-phosphono analogue has been easily converted into UDP-C-Galf. UDP-C-Galf was tested as a competitive inhibitor of UDP-galactopyranose mutase and showed inhibition of Galf formation. Thus, it is of potential interest as an antimycobacterial agent; as an active molecule against Trypanosoma cruzi, the causative agent of South American trypanosomiasis (Chagas' disease), and as a stable analogue for use in UDP-galactopyranose mutase crystallization studies.

引用

页码：6202 / 6205

页数：4

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