501088-45-5Relevant academic research and scientific papers
α- and β-Glycosyl sulfonium ions: Generation and reactivity
Nokami, Toshiki,Shibuya, Akito,Manabe, Shino,Ito, Yukishige,Yoshida, Jun-Ichi
, p. 2252 - 2255 (2009)
A study was conducted to observe the generation and reactivity of α- and β-glycosyl sulfonium ions. Preparation of a glycosyl triflate of 2-deoxy-2-amino sugar was done from a thioglycoside using glycosyl triflate pool method. The triflate oxygen was boun
Synthesis of novel triazole-derived glycopeptides as analogs of α-dystroglycan mucins
Marchiori, Marcelo Fiori,Iossi, Giulia Pompolo,Bortot, Leandro Oliveira,Dias-Baruffi, Marcelo,Campo, Vanessa Leiria
, p. 23 - 32 (2019)
α-Dystroglycan (α-DG) mucins are essential for maintenance of the structural and functional stability of the muscle fiber and, when hypoglycosylated, they are directly involved in pathological processes such as dystroglycanopathies. Thus, this work report
Automated Quantification of Hydroxyl Reactivities: Prediction of Glycosylation Reactions
Chang, Chun-Wei,Lin, Mei-Huei,Chan, Chieh-Kai,Su, Kuan-Yu,Wu, Chia-Hui,Lo, Wei-Chih,Lam, Sarah,Cheng, Yu-Ting,Liao, Pin-Hsuan,Wong, Chi-Huey,Wang, Cheng-Chung
supporting information, p. 12413 - 12423 (2021/05/03)
The stereoselectivity and yield in glycosylation reactions are paramount but unpredictable. We have developed a database of acceptor nucleophilic constants (Aka) to quantify the nucleophilicity of hydroxyl groups in glycosylation influenced by the steric, electronic and structural effects, providing a connection between experiments and computer algorithms. The subtle reactivity differences among the hydroxyl groups on various carbohydrate molecules can be defined by Aka, which is easily accessible by a simple and convenient automation system to assure high reproducibility and accuracy. A diverse range of glycosylation donors and acceptors with well-defined reactivity and promoters were organized and processed by the designed software program “GlycoComputer” for prediction of glycosylation reactions without involving sophisticated computational processing. The importance of Aka was further verified by random forest algorithm, and the applicability was tested by the synthesis of a Lewis A skeleton to show that the stereoselectivity and yield can be accurately estimated.
Chondroitin sulfate oligosaccharides and preparation method and applications thereof
-
Paragraph 0094; 0118-0120, (2019/08/06)
The invention discloses a series of chondroitin sulfate oligosaccharides as shown in a formula and a preparation method and biological activity thereof, and intermediates and a synthesis method of theintermediates. The key points of the invention are as f
Total Synthesis of the Congested, Bisphosphorylated Morganella morganii Zwitterionic Trisaccharide Repeating Unit
Keith, D. Jamin,Townsend, Steven D.
supporting information, 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.
Ligand design for somatostatin receptor isoforms 4 and 5
Negi, Arvind,Zhou, Jian,Sweeney, Sinclair,Murphy, Paul V.
supporting information, p. 148 - 159 (2018/12/04)
The somatostatin receptor (SSTR) isoforms, SSTR-4 and SSTR-5 are targets in numerous disorders and diseases. Although there has been some success in achieving selective isoform inhibition, structure-based drug design and development in this area has faced a challenge, mainly attributed to the lack of availability of SSTR-4 and SSTR-5 crystal structures. Previous structure activity relationship (SAR) studies have included work on non-peptide peptidomimetics or β-turn peptidal peptidomimetics where side chains of lysine, tryptophan, and phenylalanine (i.e. functional epitopes) are presented on a scaffold or molecular framework. However, there could be more structural information that would help design ligands selective for one or more of these isoforms. Here, we include synthesis of new mimetics and include their evaluation as ligands for SSTR-4 and SSTR-5. Inhibitors based on small to larger sized scaffolds (ManNAc, iminosugars, Eannaphane macrocycles, acyclic and cyclised peptide structures) are compared. These scaffolds have been grafted with side chains of lysine, tryptophan, and phenylalanine or similar bioisosteres/pharmacophoric groups. A new macrocycle as well as an iminosugar derivative show 5-fold or greater selectivity for SSTR-4 over SSTR-5. A new glycopeptide presenting GlcNAc showed ～6 fold selectivity for SSTR-5, which contrasted with the non-glycosylated peptide. A number of non-peptide dual inhibitors (Ki values of 0.58 μM to 5 μM) were also identified. Conceivable molecular interactions of these inhibitors were studied with newly constructed homology models of SSTR-4 and SSTR-5 isoforms.
Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity
Chang, Chun-Wei,Wu, Chia-Hui,Lin, Mei-Huei,Liao, Pin-Hsuan,Chang, Chun-Chi,Chuang, Hsiao-Han,Lin, Su-Ching,Lam, Sarah,Verma, Ved Prakash,Hsu, Chao-Ping,Wang, Cheng-Chung
supporting information, p. 16775 - 16779 (2019/11/03)
Stereocontrolled chemical glycosylation remains a major challenge despite vast efforts reported over many decades and so far still mainly relies on trial and error. Now it is shown that the relative reactivity value (RRV) of thioglycosides is an indicator for revealing stereoselectivities according to four types of acceptors. Mechanistic studies show that the reaction is dominated by two distinct intermediates: glycosyl triflates and glycosyl halides from N-halosuccinimide (NXS)/TfOH. The formation of glycosyl halide is highly correlated with the production of α-glycoside. These findings enable glycosylation reactions to be foreseen by using RRVs as an α/β-selectivity indicator and guidelines and rules to be developed for stereocontrolled glycosylation.
An Approach to Synthesize Chondroitin Sulfate-E (CS-E) Oligosaccharide Precursors
Yang, Shuang,Liu, Qi,Zhang, Guangyan,Zhang, Xiaoxi,Zhao, Zhehui,Lei, Pingsheng
, p. 5897 - 5908 (2018/05/25)
An approach was developed to synthesize chondroitin sulfate-E (CS-E) oligosaccharides by adopting a postglycosylation-transformation strategy: different from all of the traditional approaches, the characteristic groups of CS-E were introduced following the assembly of the oligosaccharides. The adjusted strategy rendered an easy chain elongation strategy. All of the elongation steps generated high yields with excellent glycosylation outcomes. An orthogonally protected disaccharide was used as the building block to provide flexibility for the group transformation and derivatization at the N-2 position of the GalNAc residue and the O-1,5 positions of the GlcA residue, thereby providing ready access for the further examination of the structure-activity relationship (SAR) of CS-E molecules.
Synthesis and anti-influenza a virus activity of 6′-amino-6′-deoxy-glucoglycerolipids analogs
Ren, Li,Zhang, Jun,Ma, Haizhen,Sun, Linlin,Zhang, Xiaoshuang,Yu, Guangli,Guan, Huashi,Wang, Wei,Li, Chunxia
, (2016/07/06)
A series of aminoglucoglycerolipids derivatives had been synthesized, including 6′-acylamido-glucoglycerolipids 1a-1f and corresponding 2′-acylamido-glucoglycerolipids 2a-2c bearing different fatty acids, glucosyl diglycerides 3a-3e bearing different func
Improvement of the stereoselectivity of the glycosylation reaction with 2-azido-2-deoxy-1-thioglucoside donors
Louren?o,Ventura
, p. 33 - 39 (2016/04/19)
2-Azido-2-deoxy-1-thioglucoside donors with an electron withdrawing group at position 6 were employed to study the stereoselectivity of the glycosylation reaction with several acceptors, ranging from unhindered small primary alcohols to other sugars and s
