Easy assembly of ligands for glycosidase affinity chromatography.
An improved, high-yield synthesis of the corresponding N-carboxypentyl derivatives of three iminoalditol glycosidase inhibitors has been developed for affinity chromatography enzyme purification. Reductive amination of 1-deoxynojirimycin (or its D-manno or D-galacto analogues) with methyl 5-formylvalerate and NaBH3CN at neutral pH afforted an aminoester which upon hydrolysis with aqueous 5% HCl gave the desired aminoacid in 97% overall yield. These amino acids could then be covalently attached using water-soluble carbodi-imide to 6-aminohexyl Sepharose 4B.
Bernotas
R C
RC
Department of Chemistry, Baker Laboratory, Cornell University, Ithaca, NY 14853.
Ganem
B
B
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives; D000447:Aldehydes; D001894:Borohydrides; D055598:Chemical Phenomena; D002621:Chemistry; D002846:Chromatography, Affinity; D003486:Cyanides; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors / Q000302:isolation & purification*; D006851:Hydrochloric Acid; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D015394:Molecular Structure
D000447:Aldehydes; D001894:Borohydrides; D003486:Cyanides; D017485:1-Deoxynojirimycin; C065663:methyl 5-formylvalerate; C065662:N-(5'-carboxypentyl)-1-deoxynojirimycin; C025364:sodium borohydride; D006026:Glycoside Hydrolases; D005944:Glucosamine; D006851:Hydrochloric Acid