In a search for a mannopyranose analogue which inhibits a-mannosidases but not a-fucosidases, ahomonojirimycin was prepared, the syntheses of 6-epi-a-homonojirimycin and of 2,6-dideoxy-2.6-imino-Lglycero-D-ralo-heptonic acid (a highly substituted pipecolic acid) are also reported.
✦ LIBER ✦
Iminoheptitols as glycosidase inhibitors: Synthesis of, and mannosidase and fucosidase inhibition by, α—homomannojirimycin and 6-epi-homomannojirimycin
✍ Scribed by Ian Bruce; George W.J. Fleet; Isabelle Cenci di Bello; Bryan Winchester
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- French
- Weight
- 280 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
C-2 and C-6 of a heptonolactone are joined together by nitrogen to afford a-homomannojirimycin (HMJ) and &epi-a-homomannojirimycin:
the inhibition of some n-mannosidases and a-fucosidases by these iminoheptitols is reported.
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## Abstract The __García‐González__ reaction of D‐glucose and ethyl acetoacetate generated ethyl 5‐[(1′__S__)‐D‐erythrosyl]‐2‐methyl‐3‐furoate (**5**), which was converted to ethyl 5‐[(1′__R__)‐1′,4′‐dideoxy‐1′,4′‐imino‐D‐erythrosyl]‐2‐methyl‐3‐furoate (**3c**) and to ethyl 5‐[(1′__S__)‐1′,4′‐dideo