CAS: 29980-16-3; Dodecyl α-D-Glucopyranoside

该化合物其结构由与葡萄糖杂质相连的多德基碳氢化合物链组成,在保持本地的相容性的同时,可以有效溶解膜蛋白.该化合物显示临界小鼠浓度(CMC)和高度生物兼容性,减少对蛋白功能的干扰.在蛋白质结晶化,电光伏和重组研究中,该物质特别宝贵.在生理条件下其稳定性和最小的腐蚀效应将其与较严的洗涤剂区分开来,因此它成为敏感应用的首选.

结构式图片

相似化合物

29781-83-7 59122-55-3 69984-73-2

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上下游产品

dodecyl 2,3,4,6-tetra-O-acetyl-α,β-D-glucopyranoside 1-dodecyl alcohol 4-nitrophenyl-β-D-galactopyranoside β-D-galactose peracetatedodecyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside dodecyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside 4)-2,3,6-tri-O-acetyl-β-D-glucopyranosidedodecyl 2,3,4,6-tetra-O-acetyl-3-O-benzyl-5a-carba-β-D-galactopyranosyl-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 4)-2,3,6-tri-O-benzyl-β-D-glucopyranosidedodecyl 3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-arabino-hex-ulopyranosyl-(1-4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

合成工艺路线路线简述

  • 合成目标产物 N-Dodecyl A-D-Glucopyranoside 主要起始原料 D-Glucose And 1-Dodecanol
  • (文献来源)合成步骤主要原料 D-Glucose 和 1-Dodecanol
📜十二烷醇置于甲醇,三氟化硼乙醚,Sodium Methylate体系中,用 二氯甲烷 用作溶剂,化学反应 40.0H,反应生成十二烷基 Alpha-D-吡喃葡萄糖苷
参考文献:(硫代)烷基六吡喃糖苷,非离子糖脂模拟物的抗微生物和细胞毒性活性.
标题:(硫代)烷基六吡喃糖苷,非离子糖脂模拟物的抗微生物和细胞毒性活性.
摘要:研究了一系列衍生自d-甘露糖,D-葡萄糖和d-半乳糖的,具有c10-C16糖苷配基的19种合成烷基和硫代烷基糖苷对7种人类癌症和2种非肿瘤细胞系的细胞毒活性以及抗菌潜力在12种细菌和酵母菌株上.发现最有效的化合物是十四烷基和十六烷基β-D-吡喃半乳糖苷(18,19),显示出对ccrf-Cem癌细胞系最佳的细胞毒性和治疗指数.相似的细胞毒活性显示十六烷基α-D-甘露吡喃糖苷(5),但它也抑制了非肿瘤细胞系.因为这两个半乳糖苷(18,19)对所有测试的细菌和酵母菌株均无活性,所以它们可能是真核细胞的靶标特异性靶标.另一方面,具有十四烷基(11)和十六烷基(12)糖苷配基的β-D-吡喃葡萄糖苷仅抑制革兰氏阳性菌粪肠球菌.从popc模型膜上的saxs实验推导,所研究的苷在高浓度下诱导脂质双层厚度和侧向相分离的变化.通常,葡糖苷和半乳糖苷表现出更具体的性质.具有较长糖苷配基的化合物显示出高细胞毒性,
Doi:10.1016/j.Carres.2019.107905

海关参考信息

专利信息


专利号:US-4739043-A
优先权日:1984-07-19
标题 :Method for the synthesis of alkyl, cycloalkyl or alcenyl aldosides or polyaldosides
发明人:DEFAYE JACQUES; WONG EMILE; PEDERSEN CHRISTIAN; CHEDIN JEAN; BOUCHU ALAIN
权利人:BEGHIN SAY SA
摘要:PCT No. PCT/FR85/00197 Sec. 371 Date Apr. 18, 1986 Sec. 102(e) Date Apr. 18, 1986 PCT Filed Jul. 18, 1985 PCT Pub. No. WO86/00906 PCT Pub. Date Feb. 13, 1986.The process comprises the action of a saturated aliphatic or cycloaliphatic alcohol or an aliphatic or cycloaliphatic alcohol comprising a double ethylenic bound not situated in alpha of the hydroxyl group with an aldose, aldoside or polyaldoside in the solvent and reactant formed by the hydrogen fluoride. Application to the synthesis of surfactants or as additives for rigidifying polyurethane foams.

专利号:US-2001049117-A1
优先权日:1998-08-20
标 题 :Analogs of udp-murnac peptides, assays, kits and related methods of their use
发明人:AXELROD HELENA R; BRANSTROM ARTHUR A
摘要:General compositions and methods for detecting Lipid I, Lipid II and peptidoglycan synthesis is disclosed. A method of screening for potential antibacterial agents is provided which requires bacterial membrane preparations or enriched enzyme preparations including at least one bacterial enzyme involved in the synthesis of Lipid I from UDP-MurNAc pentapeptide and undecaprenyl phosphate, at least one bacterial enzyme involved in the synthesis of Lipid II from Lipid I and UDP-GlcNAc and one or more bacterial enzymes involved in the further processing of Lipid II toward the downstream synthesis of peptidoglycan. The methods disclosed herein further provides a labeled UDP-MurNAc-peptide capable of serving as a substrate for a bacterial enzyme involved in the synthesis of Lipid I and a labeled UDP-GlcNAc capable of serving as a substrate for a bacterial enzyme involved in the synthesis of Lipid II. Conditions for further processing of Lipid II toward the downstream synthesis of peptidoglycan are also discribed.

专利号:US-2013243770-A1
优先权日:2005-10-14
标 题:Treating diabetes using inhibitors of il-1
发明人:LAU JESPER
权利人:NOVO NORDISK AS
摘要:The present invention describes a method of treating diabetes or metabolic syndrome with a compound that inhibits (a) IL-1, (b) the synthesis of IL-1, or (c) the release of IL-1.

专利号:WO-9713503-A1
优先权日:1995-10-13
标 题:Synthesis of drug nanoparticles by spray drying
发明人:SELVARAJ ULAGARAJ; MESSING GARY L
权利人:PENN STATE RES FOUND; SELVARAJ ULAGARAJ; MESSING GARY L
摘要:The present invention relates to a method for synthesizing nanoparticles comprising combining an agent and a matrix to form a composite mixture, and spray drying the composite mixture, wherein the nanoparticles are less than about 5000 nm. Suitable agents that can be formulated into nanoparticle in the context of the present invention include therapeutic and diagnostic agents, cosmetic, dye, photographic, food, pesticide agents, among others.

专利号:US-2015329593-A1
优先权日:2014-05-19
标题:Synthesis of Beta-Arrestin Effectors

专利号:WO-8600906-A1
优先权日:1984-07-19
标 题 :Process for the synthesis of aldosides or polyaldosides of alkyl, cycloalkyl or alkenyl

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合成参考文献


参考文献:10.1103/physreve.69.021703
摘要:Abeygunaratne S, Jákli A, Milkereit G, Sawade H, Vill V. Antiferroelectric ordering of amphiphilic glycolipids in bent-core liquid crystals. Phys Rev E Stat Nonlin Soft Matter Phys. 2004 Feb;69(2 Pt 1):021703. doi: 10.1103/physreve.69.021703.
参考文献:10.1007/s11095-016-2093-z
摘要:Kopečná M, Macháček M, Prchalová E, Štěpánek P, Drašar P, Kotora M, Vávrová K. Dodecyl Amino Glucoside Enhances Transdermal and Topical Drug Delivery via Reversible Interaction with Skin Barrier Lipids. Pharmaceutical Research. 2017 Jan 09;34(3):640–53. doi: 10.1007/s11095-016-2093-z.
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