99152-61-1Relevant academic research and scientific papers
Regioselective acetylation of diols and polyols by acetate catalysis: Mechanism and application
Ren, Bo,Rahm, Martin,Zhang, Xiaoling,Zhou, Yixuan,Dong, Hai
, p. 8134 - 8142 (2015/03/18)
We propose a principle for H-bonding activation in acylation of hydroxyl groups, where the acylation is activated by the formation of hydrogen bonds between hydroxyl groups and anions. With the guidance of this principle, we demonstrate a method for the selective acylation of carbohydrates. By this method, diols and polyols are regioselectively acetylated in high yields under mild conditions using catalytic amounts of acetate. In comparison to other methods involving reagents such as organotin, organoboron, organosilicon, organobase, and metal salts, this method is more environmentally friendly, convenient, and efficient and is also associated with higher regioselectivity. We have performed a thorough quantum chemical study to decipher the mechanism, which suggests that acetate first forms a dual H-bond complex with a diol, which enables subsequent monoacylation by acetic anhydride under mild conditions. The regioselectivity appears to originate from the inherent structure of the diols and polyols and their specific interactions with the coordinating acetate catalyst.
DesVI: A new member of the sugar N,N-dimethyltransferase family involved in the biosynthesis of desosamine
Chang, Cheng-Wei,Zhao, Lishan,Yamase, Hiroshi,Liu, Hung-Wen
, p. 2160 - 2163 (2007/10/03)
Purification and characterization of a new enzyme belonging to the amino sugar N,N-dimethyltransferase family has been achieved. DesVI catalyzes the successive transfer of two methyl groups in the biosynthetic pathway of desosamine (see scheme), an unusua
