Synthesis of L-altro-1-deoxynojirimycin, D-allo-1-deoxynojirimycin, and D-galacto-1-deoxynojirimycin from a single chiral cyanohydrin.
The chemoenzymatic synthesis of three 1-deoxynojirimycin-type iminosugars is reported. Key steps in the synthetic scheme include a Dibal reduction-transimination-sodium borohydride reduction cascade of reactions on an enantiomerically pure cyanohydrin, itself prepared employing almond hydroxynitrile lyase (paHNL) as the common precursor. Ensuing ring-closing metathesis and Upjohn dihydroxylation afford the target compounds.
van den Nieuwendijk
Adrianus M C H
AM
Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
Ruben
Mark
M
Engelsma
Sander E
SE
Risseeuw
Martijn D P
MD
van den Berg
Richard J B H N
RJ
Boot
Rolf G
RG
Aerts
Johannes M
JM
Brussee
Johannes
J
van der Marel
Gijs A
GA
Overkleeft
Herman S
HS
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D000446:Aldehyde-Lyases / Q000378:metabolism; D003500:Cyclization; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D027861:Prunus / Q000201:enzymology; D013237:Stereoisomerism
C553780:D-allo-1-deoxynojirimycin; C553779:D-galacto-1-deoxynojirimycin; C553837:L-altro-1-deoxynojirimycin; D009570:Nitriles; C430593:cyanohydrin; D017485:1-Deoxynojirimycin; D000446:Aldehyde-Lyases; C087495:acetone-cyanohydrin lyase