CAS: 10238-28-5; (2R,3R,4S,5R)-2-(4-Nitrophenoxy)Tetrahydro-2H-Pyran-3,4,5-Triol

上下游产品

4-nitro-phenol 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide 23H28ClN3O5S*C42H70O35C23H28ClN3O5S*C42H70O35 5-chloro-2-methoxy-N-(4-sulfamoylphenethyl)benzamidep-amidophenyl-α-L-arabinopyranoside p-Nitrophenyl 2,3-di-O-benzoyl-α-L-arabinopyranoside 4-nitro-phenol

📜对硝基苯酚,α-D-Xylopyranosyl Fluoride置于α-Thioglycoligase Yici-D482A Mutant体系中,用 Aq. Phosphate Buffer 用作溶剂,化学反应 4.0H,以93%的收率获得对硝基苯-Alpha-D-吡喃木糖
参考文献:α-Thioglycoligase-Based Synthesis Of O-Aryl α-Glycosides As Chromogenic Substrates For α-Glycosidases
标题:α-Thioglycoligase-Based Synthesis Of O-Aryl α-Glycosides As Chromogenic Substrates For α-Glycosidases
摘要:Alpha-Thioglycoligases Are Retaining Alpha-Glycosidase Mutants,With Modification Of Their General Acid/base Catalytic Residue To An Inactive Amino Acid Residue,Catalyzing The Formation Of S-Glycosidic Linkages Using A Sugar Donor With An Excellent Leaving Group And Suitable Sugar Acceptors With A Thiol Group As The Substrate. In This Study,We Describe The Enzymatic Synthesis Of O-Aryl Alpha-Glycosides Catalyzed By Alpha-Thioglycoligases. An Alpha-Xylosidase Mutant (Yicl-D482A) Efficiently Catalyzed The Synthesis Of O-Aryl Alpha-Xylosides In Near-Quantitative Yields (Up To 99%) Using 4-Methylumbelliferone And Nitrophenols. Synthesis Did Not occur With Those Acceptors Having A Nitro Group At The Ortho-Position. The Conversion Yields Of 3-Nitrophenol Markedly Increased At Ph 8.0,Whereas Those Of Other Aryl Compounds Were Nearly Independent Of Ph,Ranging From Ph 6.0 To 8.0. The O-Aryl Alpha-Xylosides Were Prepared On A Preparative Scale With Yields Of Up To 96%. Upon Employing The O-Aryl Alpha-Xylosides As The Substrate For The Wild-Type Yicl,Bronsted Relationships Of Log K(Cat) Versus Pk(A) And Log (K(Cat)/k-M) Versus Pk(A) Both Showed A Linear Monotonic Dependence On The Leaving Group Pk(A) With Low Beta(Lg) Values Of 0.39 And 0.38,Respectively. In Addition,Synthesis Of O-Aryl Alpha-Glucosides Was Successfully Conducted By An Alpha-Glucosidase Mutant (Mala-D416A) In The Same Fashion With High Yields. Therefore,This Strategy Can Be Used For The Synthesis Of O-Aryl Alpha-Glycosides Using An Acid/base Mutant Of Retaining Alpha-Glycosidases That Hydrolyze The Glycosides. (C) 2012 Elsevier B.V. All Rights Reserved.
Doi:10.1016/j.Molcatb.2012.10.008

专利信息

专利号:US-2007004010-A1
优先权日:2002-09-12
标题 :Engineered Enzymes and Their Use for Synthesis of Thioglycosides
发明人：WITHERS STEPHEN G; JAHN MICHAEL
权利人:UNIV BRITISH COLUMBIA
摘要:Mutant glycosidases in which the amino acid in the active site that serves as the acid, base or acid/base-catalyst is converted from a carboxylic acid to some other amino acid (for example to a simple alkyl, as in alanine or glycine) can catalyze the reaction of a thiosugar acceptor and an activated donor to form a thioglycoside. The “thioglycoligasesâ€? represent a novel class of mutant enzymes, and represent a first aspect of the invention. Thioglycoligases can be used in accordance with the method of the invention to couple a thiosugar acceptor and an activated donor to form a thioglycoside. By selection of the donor and acceptor species, as well as the specific enzyme employed, thioglycosides of different structure and stereochemistry can be obtained.

专利号:US-2006035342-A1
优先权日:2002-09-12
标 题:Engineered enzymes and their use for synthesis of thioglycosides

专利号:KR-101499065-B1
优先权日:2013-06-21
标题:Alpha-Thioglycoligase-based Synthesis of O-Aryl alpha-Glycosides

专利号:CN-102618451-B
优先权日:2011-01-28
标 题:A kind of microorganism for the synthesis of alkyl glycoside and its application

专利号:CN-102618451-A
优先权日:2011-01-28
标 题:A kind of microorganism for the synthesis of alkyl glycoside and its application

专利号:KR-20140148029-A
优先权日:2013-06-21
标题 :Alpha-Thioglycoligase-based Synthesis of O-Aryl alpha-Glycosides