Enzyme-Catalyzed Synthesis of 1-Deoxymannojirimycin, 1-Deoxynojirimycin, and 1,4-Dideoxy-1,4-imino-D-arabinitol

✍ Scribed by Dr. Thomas Ziegler; Dipl.-Chem. Alexander Straub; Prof. Dr. Franz Effenberger

• Publisher: John Wiley and Sons
• Year: 1988
• Tongue: English
• Weight: 246 KB
• Volume: 27
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.198807161

✦ Synopsis

Deoxymannojirimycin (1,5-dideoxy-1 ,S-imino-~-mannitol) 8, 1 -deoxynojirimycin (1,5-dideoxy-I ,5-iminO-D-ghcitol) 9, and 1,4-dideoxy-1,4-imino-~-arabinitol 10 are very effective glycosidase inhibitors."," The piperidine derivatives 8 and 9 have been known for some time,"] whereas the pyrrolidine derivative 10 was first discovered in 1985 in two types of leguminoses, from which it was isolated.[31 Because of their great importance as active agents a considerable number of methods have been developed for the synthesis of 8 and 9, almost all of them starting from naturally occurring carbohydrates so as to introduce as many chirality centers from the very beginning.14] Recently a synthesis of 9 from L-( +)-tartaric acid was de~cribed.'~] In the case of 10, only one synthesis has been published so far;I6'