Synthesis ofD-Allose Fatty Acid EstersviaLipase-Catalyzed Regioselective Transesterification

Abstract

The acylation of the rare sugar, D-allose (the C-3 epimer of D-glucose), with fatty acid vinyl esters was successfully carried out using Candida antarctica lipase in acetonitrile at 45 degrees C to give D-allose 6-alkanoates with high regioselectivity in good yields.

Retarding Activity of 6-O-Acyl-D-alloses against Plant Growth

“…6-O-Decanoyl-and 6-O-dodecanoyl-D-alloses (2 and 3) were prepared as reported previously, 9) and the effect of the length (C 8 -C 12 ) of the carbon chain of the fatty acid moiety on rice growth-retarding activity was investigated (Fig. 2).…”

Bovine Serum Albumin-Sugar Conjugates through the Maillard Reaction: Effects on Interfacial Behavior and Emulsifying Ability

“…Lyophilized bovine serum albumin (Fraction V, minimum 96%, product # A4503) was purchased from Sigma Chemical Co. Emulsification by BSA-sugar conjugates (GlcC8) was synthesized via regioselective esterification of D-glucose, as explained in the following section [23][24][25] . For the quantitative analysis of free amino groups of BSA-sugar conjugates, o-phthaldialdehyde (OPA) for biochemical studies was purchased from Wako Pure Chemical (Osaka).…”

“…6-O-octanoyl-D-glucose (GlcC8) was synthesized via regioselective esterification of D-glucose using octanoic acid vinyl ester as the acylating agent and lipase from Candida antarctica, Novozyme 435, immobilized on macroporous acrylic resin, as the catalyst [23][24][25] . The advantage of the vinyl ester as an acylating agent is that the enol freed by transesterfication is rapidly tautomerized into volatile acetaldehyde, thus making the process irreversible and simpler for product isolation 26) .…”

Anti-proliferative activity of 6-O-acyl-d-allose against the human leukemia MOLT-4F cell line

“…We evaluated in this present study the anti-proliferative activities of 6-O-acyl-D-alloses 12) (1-3; Fig. 1) against the human leukemia MOLT-4F cell line.…”