Dihydroxyacetone Phosphate Aldolase Catalyzed Synthesis of Structurally Diverse Polyhydroxylated Pyrrolidine Derivatives and Evaluation of their Glycosidase Inhibitory Properties

• Published in: Chemistry : a European journal Vol. 15; no. 30; pp. 7310 - 7328
• Main Authors: Calveras, Jordi, Egido‐Gabás, Meritxell, Gómez, Livia, Casas, Josefina, Parella, Teodor, Joglar, Jesús, Bujons, Jordi, Clapés, Pere
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY‐VCH Verlag 27.07.2009; Wiley
• Subjects: Aldehyde-Lyases - metabolism; Aldehydes - chemistry; aldol reaction; amino aldehydes; Catalysis; Chemistry; Chemistry, Multidisciplinary; cyclitols; Dihydroxyacetone Phosphate - chemistry; enzyme catalysis; Escherichia coli - enzymology; glycosidase inhibitors; Glycoside Hydrolases - antagonists & inhibitors; Models, Molecular; Molecular Structure; Physical Sciences; Pyrrolidines - chemical synthesis; Pyrrolidines - chemistry; Science & Technology; Stereoisomerism; aldol reaction; ASYMMETRIC-SYNTHESIS; IMINO SUGARS; CRYSTAL-STRUCTURE; enzyme catalysis; L-RHAMNOSIDASE; ALPHA-L-FUCOSIDASE; glycosidase inhibitors; MANNOSIDASE-II; CONFORMATIONAL ENERGIES; amino aldehydes; EMULSION SYSTEMS; NATURAL OCCURRENCE; cyclitols; ADDITIONS

The chemoenzymatic synthesis of a collection of pyrrolidine‐type iminosugars generated by the aldol addition of dihydroxyacetone phosphate (DHAP) to C‐α‐substituted N‐Cbz‐2‐aminoaldehydes derivatives, catalyzed by DHAP aldolases is reported. L‐Fuculose‐1‐phosphate aldolase (FucA) and L‐rhamnulose‐1‐...