93-39-0Relevant articles and documents
Biotransformation of umbelliferone by Panax ginseng root cultures
Li, Wei,Koike, Kazuo,Asada, Yoshihisa,Yoshikawa, Takafumi,Nikaido, Tamotsu
, p. 5633 - 5635 (2002)
Panax ginseng root cultures biotransformed umbelliferone (1) to its 7-O-β-D-glucopyranoside (2), 7-O-β-D-glucopyranosyl (1→6) β-D-glucopyranoside (3), 7-O-β-D-xylopyranosyl (1→6) β-D-glucopyranoside (4) and 7-O-α-L-rhamnopyranosyl (1→2) β-D-glucopyranosid
Solvent-Dependent Mechanism and Stereochemistry of Mitsunobu Glycosylation with Unprotected Pyranoses
Fujimori, Yusuke,Furuta, Takumi,Kawabata, Takeo,Nagaishi, Masaru,Sasamori, Takahiro,Shibayama, Hiromitsu,Takeuchi, Hironori,Tokitoh, Norihiro,Ueda, Yoshihiro,Yoshimura, Tomoyuki
supporting information, (2020/06/29)
An SN2 mechanism was proposed for highly stereoselective glycosylation of benzoic acid with unprotected α-d-glucose under Mitsunobu conditions in dioxane, while an SN1 mechanism was indicated for nonstereoselective glycosylation in DMF. The SN2-type stereoselective Mitsunobu glycosylation is generally applicable to various unprotected pyranoses as glycosyl donors in combination with a wide range of acidic glycosyl acceptors such as carboxylic acids, phenols, and imides, retaining its high stereoselectivity (33 examples). Glycosylation of a carboxylic acid with unprotected α-d-mannose proceeded also in an SN2 manner to directly afford a usually less accessible 1,2-cis-mannoside. One-or two-step total syntheses of five simple natural glycosides were performed using the glycosylation strategy presented here using unprotected α-d-glucose.
Exploring the catalytic promiscuity of a new glycosyltransferase from Carthamus tinctorius
Xie, Kebo,Ridao, Chen,Li, Jianhua,Wang, Ruishan,Chen, Dawei,Dou, Xiaoxiang,Dai, Jungui
supporting information, p. 4874 - 4877 (2015/04/27)
The catalytic promiscuity of a new glycosyltransferase (UGT73AE1) from Carthamus tinctorius was explored. UGT73AE1 showed the capability to glucosylate a total of 19 structurally diverse types of acceptors and to generate O-, S-, and N-glycosides, making it the first reported trifunctional plant glycosyltransferase. The catalytic reversibility and regioselectivity were observed and modeled in a one-pot reaction transferring a glucose moiety from icariin to emodin. These findings demonstrate the potential versatility of UGT73AE1 in the glycosylation of bioactive natural products.
