30319-44-9Relevant academic research and scientific papers
Synthesis of a Tridecasaccharide Lipooligosaccharide Antigen from the Opportunistic Pathogen Mycobacterium kansasii
Bai, Bing,Liu, Yu-Hsuan,Lowary, Todd L.,Shen, Ke
supporting information, p. 24859 - 24863 (2021/10/25)
The outer surfaces of mycobacteria, including the organism that causes tuberculosis, are decorated with an array of immunomodulatory glycans. Among these are lipooligosaccharides (LOSs), a class of molecules for which the function remains poorly understoo
Delta-oleanolic acid saponin compound and medical application thereof
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Paragraph 0041-0044; 0064-0068, (2020/12/31)
The invention discloses a delta-oleanolic acid saponin compound and medical application thereof. The delta-oleanolic acid saponin compound is a compound with a structural formula shown as a formula (I), and pharmaceutically acceptable salt or ester or pro
Total syntheses of schizandriside, saracoside and (±)-isolariciresinol with antioxidant activities
Sampei, Mana,Arai, Midori A.,Ishibashi, Masami
, p. 651 - 654 (2018/04/16)
Lignans are widely distributed in plants and exhibit significant pharmacological effects, including anti-tumor and antioxidative activities. Here, we describe the total synthesis of schizandriside (1), a compound we previously isolated from Saraca asoca b
Total synthesis of agalloside, isolated from: Aquilaria agallocha, by the 5-O-glycosylation of flavan
Arai, Midori A.,Yamaguchi, Yumi,Ishibashi, Masami
, p. 5025 - 5032 (2017/07/10)
Agalloside (1) is a neural stem cell differentiation activator isolated from Aquilaria agallocha by our group using Hes1 immobilized beads. We conducted the first total synthesis of agalloside (1) via the 5-O-glycosylation of flavan 25 using glycosyl fluoride 20 in the presence of BF3·Et2O. Subsequent oxidation with DDQ to flavanone 2 and deprotection successively provided agalloside (1). This synthetic strategy holds promise for use in the synthesis of 5-O-glycosylated flavonoids. The synthesized agalloside (1) accelerated neural stem cell differentiation, which is a result comparable to that for the naturally occurring compound 1.
Stereoselective Epimerizations of Glycosyl Thiols
Doyle, Lisa M.,O'Sullivan, Shane,Di Salvo, Claudia,McKinney, Michelle,McArdle, Patrick,Murphy, Paul V.
supporting information, p. 5802 - 5805 (2017/11/10)
Glycosyl thiols are widely used in stereoselective S-glycoside synthesis. Their epimerization from 1,2-trans to 1,2-cis thiols (e.g., equatorial to axial epimerization in thioglucopyranose) was attained using TiCl4, while SnCl4 promoted their axial-to-equatorial epimerization. The method included application for stereoselective β-d-manno- and β-l-rhamnopyranosyl thiol formation. Complex formation explains the equatorial preference when using SnCl4, whereas TiCl4 can shift the equilibrium toward the 1,2-cis thiol via 1,3-oxathiolane formation.
Isoquinoline-1-Carboxylate as a Traceless Leaving Group for Chelation-Assisted Glycosylation under Mild and Neutral Reaction Conditions
Wang, Hao-Yuan,Simmons, Christopher J.,Blaszczyk, Stephanie A.,Balzer, Paul G.,Luo, Renshi,Duan, Xiyan,Tang, Weiping
supporting information, p. 15698 - 15702 (2017/11/13)
Glycosyl isoquinoline-1-carboxylate was developed as a novel benchtop stable and readily available glycosyl donor. The glycosylation reaction was promoted by the inexpensive Cu(OTf)2 salt under mild reaction conditions. The copper isoquinoline-1-carboxylate salt was precipitated from the solution and thus rendered a traceless leaving group. Surprisingly, the proton from the acceptor was absorbed by the precipitated metal complex and the reaction mixture remained at neutral pH. The copper-promoted glycosylation was also proven to be completely orthogonal to the gold-promoted glycosylation, and an iterative synthesis of oligosaccharides from benchtop stable anomeric ester building blocks becomes possible under mild reaction conditions.
Uncatalyzed and chorismate mutase catalyzed claisen rearrangements of 5,6-dihydrochorismate and 6-Oxa-5,6-dihydrochorismate
Delany III, John J.,Padykula, Robert E.,Berchtold, Glenn A.
, p. 1394 - 1397 (2007/10/02)
The synthesis of 6-oxa-5,6-dihydrochorismic acid (4) from D-xylose is described. The half-lives for the uncatalyzed Claisen rearrangements of 5,6-dihydrochorismic acid (3) and 4 in D2O at 30 °C were 49000 and 1200 h, respectively, compared to a
