The University of Osaka · 생화학·유전·분자생물학
이토 유키시게 교수의 연구실은 주로 당화합물, 특히 β-맨노사이드와 같은 1,2-cis 구조를 갖는 당계 결합의 고의성 및 고선택성 합성을 목표로 합니다. 핵심 기법으로는 내재된 아실렌 도움을 받는 내분자성 당기부 전달(IAD) 전략과, 나프틸메틸(NAP) 에터, p-메톡시벤질(PMB) 등 특수 보호기군을 활용한 새로운 유기합성 전략을 개발하고 있습니다. 이는 복잡한 당쇄 구조, 특히 N-연결 당단백질의 핵심 구조인 Glc3Man1 등 고차구조 당쇄의 효율적 합성에 기여하고 있습니다.
표시된 성과는 수집된 데이터 기준으로 산출되며, 일부 차이가 있을 수 있습니다.
A simple procedure and compatibility with a variety of manipulations encountered in oligosaccharide synthesis–these advantages are features of this stereoselective synthesis of β-mannosides. The acetal 2 was obtained smoothly from the protected fluoride 1. Subsequent activation of the anomeric position afforded β-mannoside stereoselectively in good yields. CH2X = p-methoxybenzyl.
Methodology toward the stereoselective 1,2-cis glycoside linkage using intramolecular aglycon delivery (IAD) has been extensively developed. In the last two decades, progress has been made using various mixed acetal linkages and a number of glycosyl donor moieties to develop novel IAD strategies, mainly based on formation of acetal linkages. This account summarizes the newest naphthylmethyl (NAP) ether-mediated IAD as well as all the types of mediations for stereospecific construction of various
A novel use of polymer supported glycosyl donor for stereoselective synthesis of β-manno glycoside is described. This system features the use of polymer support in an unprecedented manner, in which the polymer sector serves as a “gatekeeper”. Polymer supported thiomannoside 10 that carries a p-alkoxybenzyl group as a linker at C-2 position was synthesized. This compound was subjected to the conditions of β-mannosylation according to the procedure of p-methoxybenzyl assisted intramolecular aglyco
Only a single purification step is required to isolate the glycoconjugate-related oligosaccharides prepared by a new strategy, which is shown schematically below. Prior to purification the support-bound oligosaccharide, which is labeled with a hydrophobic tag, is cleaved from the polymeric support and deprotected.
Highly efficient and stereoselective β-mannosylation was achieved by using mannosyl thioglycosides 5 and 19. Intramolecular aglycon delivery (IAD) from mixed acetal 12, 15 and 20, obtainable by oxidative coupling of aglycon onto mannosyl thio-glycosides which carry p-methoxybenzyl (PMB) group at C-2 position, was performed by the action of MeOSO2CF3 to afford β-mannosides 13/16/21. It is to be noted that efficiency of IAD was substantially improved by changing the protecting group at the 4- and
Abstract A methodology directed towards the stereoselective construction of 1,2‐ cis ‐glycosides through naphthylmethyl (NAP) ether mediated intramolecular aglycon derivery (IAD) has been developed. Stereospecific constructions of various 1,2‐ cis linkages, as in β‐mannopyrano‐, β‐arabinofurano‐, and α‐glucopyranosides, were achieved through NAP‐IAD. This methodology was successfully applied to the synthesis of Glcα(1→2)‐Glcα(1→3)‐Glcα(1→3)Man (Glc 3 Man 1 ), the nonreducing terminal structure o
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSynthetic studies on cell-surface glycans. 65. Highly stereoselective synthesis of ganglioside GD3Yukishige Ito, Masaaki Numata, Mamoru Sugimoto, and Tomoya OgawaCite this: J. Am. Chem. Soc. 1989, 111, 22, 8508–8510Publication Date (Print):October 1, 1989Publication History Published online1 May 2002Published inissue 1 October 1989https://doi.org/10.1021/ja00204a028RIGHTS & PERMISSIONSArticle Views449Altmetric-Citations85LEARN ABOUT THESE METRICSArticl
Quality control: UDP-glucose:glycoprotein glucosyltransferase (UGGT) works as the folding sensor in glycoprotein quality control. It glucosylates the Man9GlcNAc2 of misfolded glycoproteins to produce Glc1Man9GlcNAc2, which is a ligand of calnexin and calreticulin. The synthetic substrate Man9GlcNAc2-MTX can be used for the quantitative analysis of UGGT. UDP=uridine 5′-diphosphate, Glc=D-glucose, Man=D-mannose, GlcNAc=N-acetyl-D-glucosamine, MTX=methotrexate.
