Synthese von 4-Acetamido-3,7-anhydro-2-azi-1,2,4-tridesoxy-D-glycero-D-gulo-octitol, einem potentiellen Photoaffinitätsreagens mit guter Affinität zu menschlicher β-Hexosaminidase
✍ Scribed by Áts, Sándor-Csaba ;Lausberg, Elke ;Lehmann, Jochen ;Sandhoff, Konrad
- Book ID
- 102366195
- Publisher
- John Wiley and Sons
- Year
- 1990
- Tongue
- English
- Weight
- 405 KB
- Volume
- 1990
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Synthesis of 4‐Acetamido‐3,7‐anhydro‐2‐azi‐1,2,4‐trideoxy‐D‐glycero‐D‐gulo‐octitol a Good Competitive Inhibitor and Potential Photoaffinity Reagent for Human β‐Hexosaminidase
Using the known 3,4,6‐tri‐O‐acetyl‐2‐deoxy‐2‐phthalimido‐β‐D‐glucopyranosyl cyanide 2 the corresponding heptonic acid was prepared via its amide by NO~2~ treatment. Chain extension to yield 5,6,8‐tri‐O‐acetyl‐3,7‐anhydro‐1,4‐dideoxy‐4‐phthal‐imido‐D‐glycero‐D‐gulo‐oct‐2‐ulose (6) was carried out by condensing the heptonic acid chloride 5 with Meldrum's acid. Compound 6 was finally converted into 4‐acetamido‐3,7‐anhydro‐2‐azi‐1,2,4‐trideoxy‐D‐glycero‐D‐gulo‐octitol (8) by conventional methods. This compound, being an enzyme resistant analog of a glucosaminide, was shown to be a good competitive inhibitor for lysosomal β‐hexosaminidase (2‐acet‐amido‐2‐deoxy‐β‐D‐hexoside acetamidodeoxyhexohydrolase, E.C. 3.2.1.52) and a potential photoaffinity reagent.