220645-86-3Relevant academic research and scientific papers
Efficient Synthesis of Antigenic Trisaccharides Containing N-Acetylglucosamine: Protection of NHAc as NAc2
Tsutsui, Masato,Sianturi, Julinton,Masui, Seiji,Tokunaga, Kento,Manabe, Yoshiyuki,Fukase, Koichi
, p. 1802 - 1810 (2020/02/15)
The antigenic trisaccharides, α-gal epitope and H antigen, containing N-acetyl-d-glucosamine (GlcNAc) were synthesized using a diacetyl strategy, in which NHAc is tentatively converted to NAc2 during oligosaccharide construction. Acetylation of
Total Synthesis of the Congested, Bisphosphorylated Morganella morganii Zwitterionic Trisaccharide Repeating Unit
Keith, D. Jamin,Townsend, Steven D.
, p. 12939 - 12945 (2019/08/22)
Zwitterionic polysaccharides (ZPSs) activate T-cell-dependent immune responses by major histocompatibility complex class II presentation. Herein, we report the first synthesis of a Morganella morganii ZPS repeating unit as an enabling tool in the synthesis of novel ZPS materials. The repeating unit incorporates a 1,2-cis-α-glycosidic bond; the problematic 1,2-trans-galactosidic bond, Gal-β-(1 → 3)-GalNAc; and phosphoglycerol and phosphocholine residues which have not been previously observed together as functional groups on the same oligosaccharide. The successful third-generation approach leverages a first in class glycosylation of a phosphoglycerol-functionalized acceptor. To install the phosphocholine unit, a highly effective phosphocholine donor was synthesized.
Phosphotungstic acid as a novel acidic catalyst for carbohydrate protection and glycosylation
Chen, Jyun-Siao,Sankar, Arumugam,Lin, Yi-Jyun,Huang, Po-Hsun,Liao, Chih-Hsiang,Wu, Shen-Shen,Wu, Hsin-Ru,Luo, Shun-Yuan
, p. 33853 - 33862 (2019/11/11)
This work demonstrates the utilization of phosphotungstic acid (PTA) as a novel acidic catalyst for carbohydrate reactions, such as per-O-acetylation, regioselective O-4,6 benzylidene acetal formation, regioselective O-4 ring-opening, and glycosylation. These reactions are basic and salient during the synthesis of carbohydrate-based bioactive oligomers. Phosphotungstic acid's high acidity and eco-friendly character make it a tempting alternative to corrosive homogeneous acids. The various homogenous acid catalysts were replaced by the phosphotungstic acid solely for different carbohydrate reactions. It can be widely used as a catalyst for organic reactions as it is thermally stable and easy to handle. In our work, the reactions are operated smoothly under ambient conditions; the temperature varies from 0 °C to room temperature. Good to excellent yields were obtained in all four kinds of reactions.
Determining Substrate Specificities of β1,4-Endogalactanases Using Plant Arabinogalactan Oligosaccharides Synthesized by Automated Glycan Assembly
Bartetzko, Max P.,Schuhmacher, Frank,Seeberger, Peter H.,Pfrengle, Fabian
, p. 1842 - 1850 (2017/02/10)
Pectin is a structurally complex plant polysaccharide with many industrial applications in food products. The structural elucidation of pectin is aided by digestion assays with glycosyl hydrolases. We report the automated glycan assembly of oligosaccharid
Efficient one-pot per-: O -acetylation-thioglycosidation of native sugars, 4,6- O -arylidenation and one-pot 4,6- O -benzylidenation-acetylation of S -/ O -glycosides catalyzed by Mg(OTf)2
Mukherjee, Mana Mohan,Basu, Nabamita,Chaudhury, Aritra,Ghosh, Rina
, p. 109301 - 109314 (2016/11/30)
A sequential one-pot per-O-acetylation-S-/O-glycosidation of native mono and disaccharides under solvent free conditions using 0.5 mole% of Mg(OTf)2 as a non-hygroscopic, recyclable catalyst is reported. Regioselective 4,6-O-arylidenation of glycosides and thioglycosides with benzaldehyde or p-methoxybenzaldehyde dimethyl acetal is catalyzed by 10 mole% of Mg(OTf)2 to produce the corresponding 4,6-O-arylidenated product in high yields. Mg(OTf)2 can also mediate sequential one-pot benzylidenation-acetylation of mono and disaccharide based glycosides and thioglycosides in high yield.
Chemical synthesis of a heparan sulfate glycopeptide: Syndecan-1
Yang, Bo,Yoshida, Keisuke,Yin, Zhaojun,Dai, Hang,Kavunja, Herbert,El-Dakdouki, Mohammad H.,Sungsuwan, Suttipun,Dulaney, Steven B.,Huang, Xuefei
, p. 10185 - 10189,5 (2012/12/12)
Finishing first: The highly complex structure of the title compound (see picture) was assembled. The protective groups utilized, as well as the sequences for formation of the glycosyl linkages and protecting group removal are critical to the success of the synthesis. This first preparation of a heparan sulfate glycopeptide lays the foundation for accessing other members of this class of molecules. Copyright
Low-concentration 12-trans β-selective glycosylation strategy and its applications in oligosaccharide synthesis
Chao, Chin-Sheng,Li, Chen-Wei,Chen, Min-Chun,Chang, Shih-Sheng,Mong, Kwok-Kong Tony
supporting information; experimental part, p. 10972 - 10982 (2010/04/30)
This study develops an operationally easy, efficient, and general 1,2-trans β-selective glycosylation reaction that proceeds in the absence of a C2 acyl function. This process employs chemically stable thioglycosyl donors and low substrate concentrations to achieve excellent β-selectivities in glycosylation reactions. This method is widely applicable to a range of glycosyl substrates irrespective of their structures and hydroxyl-protecting functions. This low-concentration 1,2-trans β-selective glycosylation in carbohydrate chemistry removes the restriction of using highly reactive thioglycosides to construct 1,2-trans β-glycosidic bonds. This is beneficial to the design of new strategies for oligosaccharide synthesis, as illustrated in the preparation of the biologically relevant β-(1-6)-glucan trisaccharide, β-linked Gb3 and isoGb3 derivatives.
Efficient formation and cleavage of benzylidene acetals by sodium hydrogen sulfate supported on silica gel
Niu, Youhong,Wang, Ning,Cao, Xiaoping,Ye, Xin-Shan
, p. 2116 - 2120 (2008/02/09)
NaHSO4SiO2 was used as an efficient heterogeneous catalyst for both the formation and the cleavage of benzylidene acetals. This catalyst is compatible with many functional or protective groups. Under different solvent systems, either the formation or the cleavage of benzylidene acetals was carried out smoothly in excellent yields and with good chemoselectivity. Georg Thieme Verlag Stuttgart.
Stripping off water at ambient temperature: Direct atom-efficient acetal formation between aldehydes and diols catalyzed by water-tolerant and recoverable vanadyl triflate
Chen, Chien-Tien,Weng, Shiue-Shien,Kao, Jun-Qi,Lin, Chun-Cheng,Jan, Mi-Dan
, p. 3343 - 3346 (2007/10/03)
(Chemical Equation Presented) Aromatic aldehydes can be readily protected as acetals with 1,2- and 1,3-diols by using vanadyl triflate as a catalyst in CH3CN at ambient temperature. Carbohydrate-based 1,2- and 1,3-diols can similarly be protected in good to excellent yields. The catalyst can be readily recovered from the aqueous layer. In combination with vanadyl triflate-catalyzed sequential regioselective, reductive acetal opening and chemoselective acylations, the title method allows for differential functionalization of all four hydroxyl units in a given glucopyranoside.
Programmable one-pot oligosaccharide synthesis
Zhang, Zhiyuan,Ollmann, Ian R.,Ye, Xin-Shan,Wischnat, Ralf,Baasov, Timor,Wong, Chi-Huey
, p. 734 - 753 (2007/10/03)
In an effort to develop a broadly applicable approach to the facile one- pot synthesis of oligosaccharides, the reactivity of a number of p- methylphenyl thioglycoside (STol) donors which are either fully protected or have one hydroxyl group exposed has b
