Practical Production of 6-O-Octanoyl-D-allose and Its Biological Activity on Plant Growth

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

“…7) We have already reported that the growth-inhibiting activity of 6-O-octanoyl-D-allose against lettuce seedlings was about 6-fold greater than that of D-allose. 8) This significant improvement in plant growth-inhibiting activity makes it interesting to examine the retarding activities of different lengths of 6-O-acyl-D-alloses against plant growth. There is also a need to establish whether the -axial hydroxy group at C-3 in D-allose is important for this retarding activity.…”

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

“…7,11) Although why this modification increased its inhibitory activity is not fully understood, we speculate that this structural modification could be applied to enhance the anti-proliferative activity of D-allose.…”

“…7) Although D-allose has attracted attention as the functional sugar, the limited availability of this "rare" sugar from natural sources and the lack of a bulk-scale production method have hampered investigations on its mechanism of action and the development of superior analogs. A bio-production method for D-allose has recently been developed, using recombinant enzymes from bacteria, 8) which has facilitated studies on the biological activities of D-allose.…”