Methyl 2-aminotetradecanoate hydrochloride | 129938-56-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Methyl 2-aminotetradecanoate hydrochloride
• 英文别名: 2-amino-tetradecanoic acid methyl ester; hydrochloride；2-Amino-tetradecansaeure-methylester; Hydrochlorid；methyl α-aminotetradecanoate hydrochloride；α-aminomyristic acid methyl ester,HCl；Methyl 2-aminotetradecanoate;hydrochloride
• CAS: 129938-56-3
• 化学式: C₁₅H₃₁NO₂*ClH
• 分子量: 293.878
• InChiKey: XVNZEJIEGYIBLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  19
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  52.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 2-aminotetradecanoate hydrochloride 在 甲醇 、 sodium hydroxide 、 tributylcosanoyl ammonium sulphate 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 2-(2-tert-Butoxycarbonylamino-tetradecanoylamino)-tetradecanoic acid
  参考文献：
  名称：

  Gibbons, William A.; Hughes, Richard A.; Charalambous, Mario, Liebigs Annalen der Chemie, 1990, # 12, p. 1175 - 1183

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基十四烷酸 在 氯化亚砜 、 氨 作用下， 以 甲醇 为溶剂， 生成 Methyl 2-aminotetradecanoate hydrochloride
  参考文献：
  名称：

  Acylated insulin

  摘要：

  本发明涉及具有延长作用特性的人类胰岛素衍生物，其中A21和B3氨基酸残基分别为可以由遗传密码编码的任何氨基酸残基，但不能为赖氨酸、精氨酸和半胱氨酸；Phe.sup.B1 可能被删除；B30氨基酸残基为(a) 一种非可编码的亲脂性氨基酸，具有10至24个碳原子，此时一种含有最多5个碳原子的羧酸酰基与Lys.sup.B29的E-氨基团结合；(b) 任何可以由遗传密码编码的氨基酸残基，但不能为赖氨酸、精氨酸和半胱氨酸，此时一个亲脂性取代基与Lys.sup.B29的E-氨基团结合；或(c) 被删除，此时一个亲脂性取代基与LyS.sup.B29的E-氨基团结合；以及其任何Zn.sup.2+络合物；但是当B30氨基酸残基为脯氨酸或丙氨酸时，A21和B3氨基酸残基均为天冬氨酸，且Phe.sup.B1存在时，那么胰岛素衍生物为一个Zn.sup.2 +络合物。

  公开号：

  US05750497A1

文献信息

• Lipidic peptides X. Synthesis, structural and physico-chemical elucidation of lipidic amino acid conjugates with hydrophilic compounds
  作者：Istvan Toth、Graeme J. Anderson、Rohanah Hussain、Ian P. Wood、Esther del Olmo Fernandez、Peter Ward、William A. Gibbons

  DOI：10.1016/s0040-4020(01)88194-1

  日期：——

  Lipidic amino acids 1a, c and dimer 1b were coupled to highly hydrophilic compounds, lactic, glycolic and gluconic acids and protected gulonic acid, yielding conjugates 1d,f,h,i,j,l and o. After carboxyl deprotection, acids e,g and m and were obtained. Physico-chemical investigations of these compounds were carried out using proton nuclear magnetic resonance. Plots of chemical shift versus concentration

  脂质氨基酸1a，c和二聚体1b与高度亲水的化合物，乳酸，乙醇酸和葡萄糖酸以及受保护的古洛糖酸偶联，得到缀合物1d，f，h，i，j，l和o。羧基脱保护后，得到酸e，g和m 1和m。使用质子核磁共振对这些化合物进行了物理化学研究。化学位移对浓度的图揭示了在高浓度下形成聚集体或胶束而在低浓度下形成单体。
• Hussain, Rohanah; Toth, Istvan; Gibbons, William A., Liebigs Annalen der Chemie, 1991, # 9, p. 963 - 966
  作者：Hussain, Rohanah、Toth, Istvan、Gibbons, William A.

  DOI：——

  日期：——
• Unsymmetrical Azo Initiators Increase Efficiency of Radical Generation in Aqueous Dispersions, Liposomal Membranes, and Lipoproteins
  作者：Sean M. Culbertson、Ned A. Porter

  DOI：10.1021/ja9934605

  日期：2000.5.1

  Lipid peroxidation studies often employ the use of azo initiators to produce a slow, steady source of free radicals, but the lack of initiators capable of efficiently generating radicals in lipid aggregates such as micelles and membranes has created persistent problems in these investigations. We report here the synthesis and study of unsymmetrically substituted (hydrophilic/hydrophobic) azo initiators C-8, C-12, and C-16 that increase the efficiency of radical generation in lipophilic regions of aqueous emulsions such as micelles and liposomes. Radical generation from these initiators was monitored in micelles? liposomes, and lipoproteins by the use of two radical scavengers, one that scavengers lipophilic peroxyl radicals and one that scavenges hydrophilic peroxyls. The lipophilic radical scavenger used was the well-known antioxidant alpha-tocopherol and thr hydrophilic radical scavenger used was uric acid. Two peroxyl radicals are trapped by each of these scavengers, tocopherol presumably being biased toward reacting with lipid soluble radicals, uric acid presumably reacting preferentially with water-soluble radicals. In Triton X-100 micelles the unsymmetrical initiators C-8 and C-16 display an increase in both alpha-TOH (alpha-tocopherol) trapping and in overall radical generation efficiency compared to the symmetrical initiators C-0 (hydrophilic) and MeOAMVN (lipophilic). The unsymmetrical azo initiators performance in liposomes was excellent (increased cage escape with lipid compartment access). In low-density lipoprotein oxidations, the initiators C-8, C-12, and C-16 also provided advantages over C-0 and MeOAMVN. The hydrophilic/hydrophobic character of the two radicals generated from the unsymmetrical initiators is an important factor for separating the geminate radical pair, These initiators, when compared to the widely used symmetrical azo initiators, provide an advantage of free radical production, lipophilic access, and constant radical generation in the investigation of lipid peroxidation in various media.
• Abderhalden; Tanaka, Fermentforschung, vol. 7, p. 155
  作者：Abderhalden、Tanaka

  DOI：——

  日期：——
• Lipophilic methotrexate conjugates with antitumor activity
  作者：Rosario Pignatello、Giuseppina Spampinato、Valeria Sorrenti、Claudia Di Giacomo、Luisa Vicari、John J McGuire、Cynthia A Russell、Giovanni Puglisi、Istvan Toth

  DOI：10.1016/s0928-0987(00)00062-2

  日期：2000.5

  Lipophilic methotrexate (MTX)-lipoamino acid conjugates coupled with amide or ester Linkages (1a-1r) were synthesised. The inhibitory activity of the conjugates was evaluated on bovine Liver DHFR. The in vitro growth inhibitory effect against MTX-sensitive human lymphoblastoid CCRF-CEM cells and an MTX-resistant sub-line (CEM/MTX), which displays defective intracellular transport of MTX, was determined under short-term and continuous (120-h incubation) exposure conditions. The alpha, gamma, or alpha,gamma amide conjugates showed different activity in inhibiting the growth of parent cells. CEM/MTX cells were much less susceptible than CCRF-CEM cells to inhibition by alpha or alpha,gamma-substituted lipoamino acid conjugates, whereas both cell lines were almost equally sensitive to the MTX-gamma conjugates. Although less potent than MTX, they could partially circumvent the impaired transport system. These findings confirm that lipophilic MTX conjugates may be good lead compounds on the drug development for the treatment of some MTX-resistant tumors. Ester-type conjugates displayed an interesting activity against parent CCRF-CEM cells, although they were less potent against the transport-resistant sub-line. Stability studies on these molecules indicated that they are not degraded into MTX in the culture medium, thus suggesting that they are not able to over-cross cell resistance despite of their lipophilicity. (C) 2000 Elsevier Science B.V. All rights reserved.