methyl (2-amino-4-mercapto)-butyrate | 764724-33-6

• 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-amino-4-mercapto)-butyrate
• 英文别名: homocysteine methyl ester；2-amino-4-mercapto-butyric acid methyl ester；Methyl 2-amino-4-sulfanylbutanoate
• CAS: 764724-33-6
• 化学式: C₅H₁₁NO₂S
• 分子量: 149.214
• InChiKey: GPBQMUGQGMBCNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  211.1±30.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  53.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2-amino-4-mercapto)-butyrate 在 三乙胺 作用下， 生成 4-(4-Bromo-benzylsulfanyl)-2-tert-butoxycarbonylamino-butyric acid methyl ester
  参考文献：
  名称：

  氨基酸衍生的二氧化硫和二氧化锡系统作为一次性模板：α-氨基酮，抗氨基醇和氨基环戊烯酮的合成

  摘要：

  由甲硫氨酸和高半胱氨酸硫代内酯合成的砜和亚砜已使用双（三甲基甲硅烷基）氨基钾环化成氨基酮。用一种砜进行Ramberg-Bäcklund化学反应可得到氨基环戊烯酮，而无环α-氨基酮和抗氨基醇则是通过阮内镍对亚砜进行脱硫而得到的。

  DOI：

  10.1016/0040-4039(96)01610-3
• 作为产物：
  描述：

  DL-高半胱氨酸硫内酯盐酸盐 、 sodium methylate 反应 0.5h， 生成 methyl (2-amino-4-mercapto)-butyrate
  参考文献：
  名称：

  Rationally engineered variants of S-adenosylmethionine (SAM) synthase: reduced product inhibition and synthesis of artificial cofactor homologues

  摘要：

  通过三维建模和对接，对细菌腺苷甲硫氨酸合成酶进行合理重设计，导致产生变种，可以合成甲基化辅酶SAM（AdoMet）而无产物抑制，并且可以合成更高级的烷基同系物。

  DOI：

  10.1039/c4cc08478k

文献信息

• [EN] SPIROCYCLIC DEGRONIMERS FOR TARGET PROTEIN DEGRADATION<br/>[FR] DÉGRONIMÈRES SPIROCYCLIQUES POUR LA DÉGRADATION DE PROTÉINES CIBLES
  申请人：C4 THERAPEUTICS INC

  公开号：WO2017197036A1

  公开（公告）日：2017-11-16

  This invention provides compounds that have spirocyclic E3 Ubiquitin Ligase targeting moieties (Degrons), which can be used as is or linked to a targeting ligand for a protein that has been selected for in vivo degradation, and methods of use and compositions thereof as well as methods for their preparation.

  这项发明提供了具有螺环式E3泛素连接酶靶向基团（Degrons）的化合物，这些化合物可以直接使用，也可以与靶向配体连接，用于选定用于体内降解的蛋白质，并提供了使用方法、组合物以及其制备方法。
• Synthesis and in vitro antitumor effect of diclofenac and fenoprofen thiolated and nonthiolated polyaspartamide-drug conjugates
  作者：M. Barbarić、M. Kralj、M. Marjanović、I. Husnjak、K. Pavelić、J. Filipović-Grčić、D. Zorc、B. Zorc

  DOI：10.1016/j.ejmech.2006.08.009

  日期：2007.1

  This paper reports the synthesis and antiproliferative effects of new thiomer-diclofenac and fenoprofen conjugates, hydrophilic, bioadhesive, polymeric prodrugs, as well as antiproliferative effects of diclofenac, fenoprofen and a series of previously described polymer-fenoprofen conjugates on five tumor cell lines. Thiolated and nonthiolated polyaspartamides were the chosen polymeric components. Drug-loading ranged from 5.6 to 22.4%, and the amount of SH groups ranged from 6.9 to 45.6 mu mol g(-1). Tensile studies demonstrated a clear correlation between the amount of thiol and the mucoadhesive properties of the conjugates. The growth-inhibitory activity of the tested polymer-drug conjugates demonstrates that polyaspartamide-type polymers, especially thiolated polymers, enable inhibition of tumor cell growth with significantly lower doses of the active substance. (c) 2006 Elsevier Masson SAS. All rights reserved.
• Szesni, Normen; Hohberger, Christiane; Mohamed, Gehad Genidy, Journal of Organometallic Chemistry, 2006, vol. 691, p. 5753 - 5766
  作者：Szesni, Normen、Hohberger, Christiane、Mohamed, Gehad Genidy、Burzlaff, Nicolai、Weibert, Bernhard、Fischer, Helmut

  DOI：——

  日期：——
• Rationally engineered variants of S-adenosylmethionine (SAM) synthase: reduced product inhibition and synthesis of artificial cofactor homologues
  作者：M. Dippe、W. Brandt、H. Rost、A. Porzel、J. Schmidt、L. A. Wessjohann

  DOI：10.1039/c4cc08478k

  日期：——

  Rational redesign of bacterialS-adenosylmethionine-synthase by 3D-modelling and docking led to variants that allow synthesis of methylation cofactor SAM (AdoMet) without product inhibition, and of higher alkyl homologues.

  通过三维建模和对接，对细菌腺苷甲硫氨酸合成酶进行合理重设计，导致产生变种，可以合成甲基化辅酶SAM（AdoMet）而无产物抑制，并且可以合成更高级的烷基同系物。
• Amino acid derived thiane oxide and dioxide systems as disposable templates: Synthesis of α-amino ketones, anti-amino alcohols and an amino cyclopentenone
  作者：Mark P. Gamble、Gerard M.P. Giblin、John G. Montana、Peter O'Brien、Timothy P. Ockendon、Richard J.K. Taylor

  DOI：10.1016/0040-4039(96)01610-3

  日期：1996.10

  Sulfones and sulfoxides synthesised from methionine and homocysteine thiolactone have been cyclised to amino ketones using potassium bis(trimethylsily)amide. Ramberg-Bäcklund chemistry on one of the sulfones gave an amino cyclopentenone whereas acyclic α-amino ketones and anti-amino alcohols were obtained by Raney nickel desulfurisation of the sulfoxides.

  由甲硫氨酸和高半胱氨酸硫代内酯合成的砜和亚砜已使用双（三甲基甲硅烷基）氨基钾环化成氨基酮。用一种砜进行Ramberg-Bäcklund化学反应可得到氨基环戊烯酮，而无环α-氨基酮和抗氨基醇则是通过阮内镍对亚砜进行脱硫而得到的。