Photobromination of a rigid bicyclic ~t-L-fucose analogue, affords a single crystalline monobromide, the structure of which is confirmed by X-ray crystallography. Displacement of this bromide with azide proceeds with inversion to a single crystalline azide, which on reduction leads to an amine and t
Inhibition of Fucosyl Transferase and Fucosidase by a Rigid Bicyclic Mimic of α-L-Fucose
✍ Scribed by Annabel R Beacham; Kathryn H Smelt; Keith Biggadike; Christopher J Britten; Lucy Hackett; Bryan G Winchester; Robert J Nash; Rhodri C Griffiths; George W.J Fleet
- Book ID
- 104258445
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 801 KB
- Volume
- 39
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A rigidbicyclic analogge of a-L-fpcose, prepsred from a monoacetonide of Lgulonolactone in an overatl yield of 36% with6utthe need fti. cohmm chromatography,is a potentinhibitorof fueoaidases~d a weak inhibitorof a fucosyl transferaae. r?) 1997ElwvierScienceLtd. Allrightsresewed.
Analogues of L-fhcoae1 mayinhibitenzymeswhich hydrolyse(fucosida&e)l or make (fucosyl, twnsferases)' oligosaccharides, or may bind to receptorswhich are importantcornpdnentsof cell-cellrecognitionsuch as Lewis X.3Thereare anenormousnumberof potentialapplicatlmgofmaterialsthat havesp=ific intet'=tionsin anyof thesebiological pmcesaes,not onlyas potentiti chemothdqe utic agentsbut more certainlyas probes forthe understandingof a numberof processesin whichthe imndominant sugarL-fucow is involved.'
📜 SIMILAR VOLUMES
Photobromination of the rigid aza-bicyclic fucose mimic 3 gave a reactive type bromide 7 as a divergent intermediate for the synthesis of both 7-O and 7-8 yinked 1 cosyl bicyclic L-fucose derivatives by direct displacement with alcohols or amines. Displacement of the bromide 7 with sodium azide gave