CAS: 85618-21-9; (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(Octylthio)Tetrahydro-2H-Pyran-3,4,5-Triol

该化合物是生物化学和生物物理研究中广泛使用的,用于膜蛋白溶解和稳定化的非离子硫基二醇表面活性剂,其主要优点包括轻度的洗涤剂特性,高纯度和与敏感蛋白结构的兼容性,使之适合蛋白结晶和重组研究等应用; 硫基二醇联系与传统的胶层相比,增强了化学稳定性,减少了水解风险; 其辛基链条长度在水利疏离和水利生物相互作用之间提供了最佳平衡,促进了高效的膜蛋白蛋白提取,同时尽量减少了衰化; 化合物在结构生物学和酶学中特别宝贵,因为它有能力保持蛋白的溶解功能.

结构式图片

相似化合物

7473-36-1 13533-58-9 367-93-1

上下游产品

β-thio°Ctylperacetyl D-glucoside 1-bromo-°Ctane 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiouronium bromide 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide°Ctyl 4,6-O-benzylidene-β-D-thioglucopyranoside °Ctyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-1-thioglucopyranoside 2-hexyl-1-°Ctyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 2-hexyl-1-°Ctyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside

合成工艺路线路线简述

  • 85618-26-4 = 85618-21-9
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Methanol
    标题:Synthesis Of Alkyl-β-D-Thioglucopyranosides,A Series Of New Nonionic Detergents
    作者:Saito,Setsuo; Et Al
    参考文献:Chemical & Pharmaceutical Bulletin 日期:1985 卷标:33(2) 页码:503-8]

    604-69-3 = 85618-21-9 + 128731-75-9
    反应条件:1.1 Reagents: Boron Trifluoride Etherate Solvents: Chloroform2.1 Reagents: Boron Trifluoride Etherate Solvents: Chloroform
    标题:Synthesis And Liquid Crystalline Properties Of The N-Alkyl 1-Thio-α-D-Glucopyranosides,A New Homologous Series Of Carbohydrate Mesogens
    作者:Van Doren,Henk A.; Et Al
    参考文献:Carbohydrate Research 日期:1989 卷标:194 页码:71-7]

    604-69-3 = 85618-21-9
    反应条件:1.1 Catalysts: Indium Tribromide Solvents: Chloroform; Rt -> Reflux; 1 H,Reflux1.2 Catalysts: Sodium Methoxide Solvents: Methanol; 16 H,Ph 9,Rt1.3 Reagents: Dowex; Acidified,Rt
    标题:Preparation Of S-Glycoside Surfactants And Cysteine Thioglycosides Using Minimally Competent Lewis Acid Catalysis
    作者:Szabo,Lajos Z.; Et Al
    参考文献:Carbohydrate Research 日期:2016 卷标:422 页码:1-4]

    85618-26-4 = 85618-21-9
    反应条件:1.1 Catalysts: Sodium Methoxide Solvents: Methanol; 16 H,Ph 9,Rt1.2 Reagents: Dowex; Acidified,Rt
    标题:Preparation Of S-Glycoside Surfactants And Cysteine Thioglycosides Using Minimally Competent Lewis Acid Catalysis
    作者:Szabo,Lajos Z.; Et Al
    参考文献:Carbohydrate Research 日期:2016 卷标:422 页码:1-4]

    40591-65-9 + 111-83-1 = 85618-21-9
    反应条件:1.1 Reagents: Potassium Carbonate,Sodium Bisulfite Solvents: Acetone,Water2.1 Reagents: Sodium Hydroxide Solvents: Methanol
    标题:Synthesis Of Alkyl-β-D-Thioglucopyranosides,A Series Of New Nonionic Detergents
    作者:Saito,Setsuo; Et Al
    参考文献:Chemical & Pharmaceutical Bulletin 日期:1985 卷标:33(2) 页码:503-8]

    572-09-8 = 85618-21-9
    反应条件:1.1 Solvents: Acetone2.1 Reagents: Potassium Carbonate,Sodium Bisulfite Solvents: Acetone,Water3.1 Reagents: Sodium Hydroxide Solvents: Methanol
    标题:Synthesis Of Alkyl-β-D-Thioglucopyranosides,A Series Of New Nonionic Detergents
    作者:Saito,Setsuo; Et Al
    参考文献:Chemical & Pharmaceutical Bulletin 日期:1985 卷标:33(2) 页码:503-8]

    604-68-2 = 85618-21-9
    反应条件:1.1 Reagents: Phosphorus,Bromine Solvents: Acetic Anhydride1.2 Reagents: Hydrogen Bromide Solvents: Water2.1 Solvents: Acetone3.1 Reagents: Potassium Carbonate,Sodium Bisulfite Solvents: Acetone,Water4.1 Reagents: Sodium Hydroxide Solvents: Methanol
    标题:Synthesis Of Alkyl-β-D-Thioglucopyranosides,A Series Of New Nonionic Detergents
    作者:Saito,Setsuo; Et Al
    参考文献:Chemical & Pharmaceutical Bulletin 日期:1985 卷标:33(2) 页码:503-8]

    85618-26-4 = 85618-21-9 + 128731-75-9
    反应条件:1.1 Reagents: Boron Trifluoride Etherate Solvents: Chloroform
    标题:Synthesis And Liquid Crystalline Properties Of The N-Alkyl 1-Thio-α-D-Glucopyranosides,A New Homologous Series Of Carbohydrate Mesogens
    作者:Van Doren,Henk A.; Et Al
    参考文献:Carbohydrate Research 日期:1989 卷标:194 页码:71-7]

    50-99-7 + 94805-33-1 = 85618-21-9 + 128731-75-9
    反应条件:1.1 Reagents: Trifluoroacetic Acid Solvents: Trifluoroacetic Acid,Water
    标题:Preparation Of Thioglycosides
    参考文献:European Patent Organization
辛基 2,3,4,6-四-O-乙酰基-Beta-D-硫代吡喃葡萄糖苷置于sodium Methylate体系中,用 甲醇 作为反应溶剂,化学反应 16.0H,反应生成 辛基-Beta-D-硫代吡喃葡萄糖苷
参考文献:使用最小感受态路易斯酸催化制备 S-糖苷表面活性剂和半胱氨酸硫糖苷.
标题:使用最小感受态路易斯酸催化制备 S-糖苷表面活性剂和半胱氨酸硫糖苷.
摘要:在这里,我们报告了一种从相应的过乙酸盐供体制备异头纯β-S-吡喃糖苷(1,2-反式糖苷)的方法.在催化量的 Inbr3 存在下,在 Chcl3 中回流进行 S-糖基化.在 Zemplen 条件下实现中间体过乙酸酯的脱酰化.五个吡喃糖的例子,单糖 D-葡萄糖和 D-半乳糖和二糖纤维二糖,麦芽糖和乳糖,被用作供体,五种硫醇,包括 α/ω 二硫醇和 Fmoc-L-半胱氨酸被用作受体.报告了先前未描述的化合物的熔点,高分辨率 Ms,αd 和 NMR 数据((1)H 和 (13)C,包括 Cosy,Hsqc 和 Hmbc).
DOI:10.1016/j.Carres.2015.12.008

海关参考信息

专利信息


专利号:US-2012190064-A1
优先权日:2004-10-01
标题 :Feeding buffers, systems, and methods for in vitro synthesis of biomolecules
发明人:KUDLICKI WIESLAW ANTONI; KEPPETIPOLA SHIRANTHI; FLETCHER JULIA; GETBEHEAD ASHLEY ELAINE; KATZEN FEDERICO; VOZZA-BROWN LAURA
权利人:KUDLICKI WIESLAW ANTONI; KEPPETIPOLA SHIRANTHI; FLETCHER JULIA; GETBEHEAD ASHLEY ELAINE; KATZEN FEDERICO; VOZZA-BROWN LAURA; LIFE TECHNOLOGIES CORP
摘要:Compositions, methods and kits for in vitro systems for synthesis of biomolecules such as polypeptides, are provided herein. Cell extracts that provide enhanced yields of soluble proteins using in vitro protein synthesis methods are provided. The invention also includes methods for producing high yields of proteins by the addition of a feeding solution that includes amino acids and an energy source to an ongoing in vitro synthesis system. The invention also includes methods of using a high-yield in vitro synthesis system to produce large quantities of proteins with incorporated labeled amino acids for analysis by methods such as by NMR. The invention further includes vectors for enhanced production of proteins from nucleic acid templates using in vitro synthesis systems.

专利号:WO-2024130393-A1
优先权日:2022-12-21
标 题 :Nanoparticle and method of synthesis thereof
发明人:MOSKOVCHENKO SVITLANA
权利人:MOSKOVCHENKO SVITLANA
摘要:The present technology relates to nanoparticles, compositions comprising said nanoparticles, and methods of synthesis of said nanoparticles; wherein the nanoparticles comprise a metal nanoparticle core, a first coating of amphiphilic molecules, and a second coating of essential oil, essential oil primary constituent, or both, which combine the antimicrobial properties of metal nanoparticles, amphiphilic molecules, and essential oil or essential oil primary constituents.

专利号:US-8067204-B2
优先权日:2005-12-15
标 题 :Long-chain chondroitin sugar chain and method for producing the same and method for promoting synthesis of chondroitin
发明人:SUGIURA NOBUO; SHIMOKATA SATOSHI; KIMATA KOJI
权利人:SUGIURA NOBUO; SHIMOKATA SATOSHI; KIMATA KOJI; SEIKAGAKU KOGYO CO LTD
摘要:A method for producing a chondroitin sugar chain comprises reacting a glucuronic acid donor, an N-acetyl galactosamine donor, a sugar receptor and a bacterial cell enzyme which synthesizes chondroitin in the presence of a surfactant. The surfactant is selected from polyoxyethylene octadecyl amine, n-decanoyl-N-methylglucamide, sodium cholate, n-octyl-β-D-thioglucopyranoside, n-nonyl-β-D-thiomaltopyranoside, sucrose monocholate, sucrose monocaprate, and sucrose monolaurate. The chondroitin sugar chain has all the following properties: a weight average molecular weight: 50,000 or more when measured by gel filtration chromatography; it is completely degraded to disaccharides with chondroitinase ABC; and when the sugar chain is decomposed with chondroitinase ABC and the decomposed products are subjected to a disaccharide analysis, substantially all of them correspond to an unsaturated disaccharide unit of chondroitin.

专利号:US-11618777-B2
优先权日:2015-07-31
标 题 :Method of manufacturing membrane protein and utilization thereof
发明人:YOKOYAMA SHIGEYUKI; SHINODA TAKEHIRO; ITO KAORI; NOMURA NAOKO; KATSURA YOSHIKO; SOMEYA TOMOMI; SHIROUZU MIKAKO; HORI TETSUYA; NAKAMURA YOSHIHIRO; TANABE HIROAKI
权利人:YOKOYAMA SHIGEYUKI
摘要:In order to provide a membrane protein production method which does not require the step of solubilizing a membrane protein and which allows the membrane protein having an excellent quality to be obtained with a high yield, a method in accordance with an embodiment of the present invention includes: a step (a) of preparing a reaction solution for cell-free protein synthesis, the reaction solution containing (i) a template nucleic acid which encodes the membrane protein, (ii) a lipid, and (iii) a detergent which is contained at a concentration equal to or higher than a critical micelle concentration; and a step (b) of synthesizing the membrane protein while the concentration of the detergent in the reaction solution is maintained at a concentration equal to or higher than a critical micelle concentration.

专利号:US-7282337-B1
优先权日:2006-04-14
标题:Methods for increasing accuracy of nucleic acid sequencing
发明人:HARRIS TIMOTHY D
权利人:HELICOS BIOSCIENCES CORP
摘要:The invention provides methods for improving the accuracy of a sequencing-by-synthesis reaction by sequencing at least a portion of a template and at least a portion of template complementary sequence.

专利号:US-2009263867-A1
优先权日:2005-12-15
标 题 :Long-chain chondroitin sugar chain and method for producing the same and method for promoting synthesis of chondroitin
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✅ COA系统入驻 | 共享模式

主要参考文献

[参考文献]: Saito S, Et Al. Characteristics Of N-Octyl Beta-D-Thioglucopyranoside, A New Non-Ionic Detergent Useful For Membrane Biochemistry. Biochem J. 1984 Sep 15;222(3):829-32.
[参考文献]: C Carnero Ruiz, Et Al. Characterization Of Mixed Non-Ionic Surfactants N-Octyl-β-D-Thioglucoside And Octaethylene-Glycol Monododecyl Ether: Micellization And Microstructure. J Colloid Interface Sci. 2011 Sep 1;361(1):178-85.
[参考文献]: Donald R Ronning, Et Al. Mycobacterium Tuberculosis Antigen 85A And 85C Structures Confirm Binding Orientation And Conserved Substrate Specificity. J Biol Chem. 2004 Aug 27;279(35):36771-7.
[参考文献]: E Yang-Boja, Et Al. Electrospray Mass Spectra Of Three Proprietary Detergents. Anal Biochem. 2000 Oct 15;285(2):205-10.
[参考文献]: Gabriella M Santonicola, Et Al. Mixtures Of N-Octyl-Beta-D-Glucoside And Triethylene Glycol Mono-N-Octyl Ether: Phase Behavior And Micellar Structure Near The Liquid-Liquid Phase Boundary. Langmuir. 2005 Oct 25;21(22):9955-63.

合成参考文献


参考文献:10.1007/s002329900533
摘要:Takeda K, Ushimaru M, Fukushima Y, Kawamura M. Characterization of a P-type Copper-Stimulated ATPase from Mouse Liver. The Journal of Membrane Biology. 1999 Jul;170(1):13–6. doi: 10.1007/s002329900533.
参考文献:10.1038/nature10136
摘要:Lebon G, Warne T, Edwards PC, Bennett K, Langmead CJ, Leslie AG, Tate CG. Agonist-bound adenosine A2A receptor structures reveal common features of GPCR activation. Nature. 2011 May 18;474(7352):521–5.
参考文献:10.1016/s0076-6879(03)73008-0
摘要:Westerman LE, Jensen PE. Liposomes composed of reconstituted membranes for induction of tumor-specific immunity. Methods Enzymol. 2003;373():118–27. doi: 10.1016/s0076-6879(03)73008-0.
参考文献:10.1007/s00425-003-1182-5
摘要:Blumenthal SS, Clark GB, Roux SJ. Biochemical and immunological characterization of pea nuclear intermediate filament proteins. Planta. 2004 Apr;218(6):965–75. doi: 10.1007/s00425-003-1182-5.
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