(6R,7R)-1-aza-3-methyl-7-(m-carboxypentanamido)-8-oxo-5-thiabicyclo<4.2.0>oct-2-ene carboxylic acid | 80154-48-9

• 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: (6R,7R)-1-aza-3-methyl-7-(m-carboxypentanamido)-8-oxo-5-thiabicyclo<4.2.0>oct-2-ene carboxylic acid
• 英文别名: 7-aminodeacetoxycephalosporanic acid；adipyl-7-aminodesacetoxycephalosporanic acid；(6R,7R)-1-aza-3-methyl-7-(m-carboxypentanamido)-8-oxo-5-thiabicyclo[4.2.0]oct-2-ene carboxylic acid；(6R,7R)-7-(5-carboxypentanoylamino)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 80154-48-9
• 化学式: C₁₄H₁₈N₂O₆S
• 分子量: 342.373
• InChiKey: CSGFFYNMTALICU-ZWNOBZJWSA-N

物化性质

• 沸点：
  763.5±60.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  149
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (6R,7R)-1-aza-3-methyl-7-(m-carboxypentanamido)-8-oxo-5-thiabicyclo<4.2.0>oct-2-ene carboxylic acid 在 immobolised penicillin acylase 作用下， 生成 7-氨基-3-甲基-8-氧代-5-硫杂-1-氮杂双环[4.2.0]辛-2-烯-2-甲酸
  参考文献：
  名称：

  [EN] PROCESS FOR THE PRODUCTION OF CEPHALOSPORINS
  [FR] PROCÉDÉ DE PRODUCTION DE CÉPHALOSPORINES

  摘要：

  本发明涉及一种组合物，其包含≥85重量％的N-去酰基头孢菌素，制备该组合物的方法以及使用所述N-去酰基头孢菌素制备高度纯化的半合成头孢菌素。

  公开号：

  WO2012032040A1
• 作为产物：
  描述：

  (2S,5R,6R)-1-aza-3,3'-dimethyl-6-(5-carboxypentanamido)-7-oxo-4-thiabicyclo<3.2.0>heptane-2-carboxylic acid 在 ring expansion enzyme from Cephalosporium CO₇₂₈ 、 氧气 、 2-氧代-戊二酸离子(2-) 、 iron(II) sulfate 、 维生素 C 、 1,4-二巯基-2,3-丁二醇 作用下， 以40%的产率得到(6R,7R)-1-aza-3-methyl-7-(m-carboxypentanamido)-8-oxo-5-thiabicyclo<4.2.0>oct-2-ene carboxylic acid
  参考文献：
  名称：

  青霉素到头孢菌素的酶促环扩展：侧链特异性

  摘要：

  青霉素的酰基氨基侧链上的结构变体，作为顶头孢霉CO728扩环酶的底物，表明除羧基端的δ-（L -α-氨基二聚体）外，六个羧基端的碳链可以有效地转化为phe烯[5-（5S）-氨基-5-羧基戊酰基]。

  DOI：

  10.1039/c39870000374

文献信息

• The emzymatic ring expansion of penicillins to cephalosporins : side chain specificity
  作者：Jack E. Baldwin、Robert M. Adlington、M.James Crabbe、Graham Knight、Takashi Nomoto、Christopher J. Schofield、Hong-Hoi Ting

  DOI：10.1016/s0040-4020(01)86840-x

  日期：1987.1

  Structural variants of the acylamino side chain of penicillins have been tested as substrates for Deacetoxy/Deacetyl Cephalosporin C Synthetase from CO 728. A six carbon chain terminating in a carboxyl group was found to permit efficient ring expansion to cephems, with the exception of δ-(-α-aminoadipoyl).1

  已经测试了青霉素的酰基氨基侧链的结构变异体作为来自CO 728的脱乙酰氧基/脱乙酰基头孢菌素C合成酶的底物。发现一个终止于羧基的6个碳链可以使环有效地扩环到头孢烯，但δ- （-α-氨基己二酰基）。1个
• Kinetic resolutions of racemic amines and alcohols catalyzed by an industrial glutaryl-7-aminocephalosporanic acid acylase with unexpected broad substrate specificity
  作者：Stefano Raimondi、Luca Forti、Daniela Monti、Sergio Riva

  DOI：10.1016/s0957-4166(03)00171-x

  日期：2003.5

  An industrial glutaryl-7-aminocephalosporanic acid acylase (GAR) possesses a significant broad substrate specificity that crosses over the usual cephalosporanic skeleton. Enantioselective amidase and even esterase activities have been observed with all the glutarates of racemic substrates investigated, with a stereopreference for the (S)-enantiomer. The different physical-chemical properties of reagents and products allow their easy separation by solvent extraction, avoiding cumbersome chromatography or distillation processes during reaction work-up. (C) 2003 Elsevier Science Ltd. All rights reserved.
• On the substrate preference of glutaryl acylases
  作者：Elena Rosini、Claudia Stella Monelli、Loredano Pollegioni、Sergio Riva、Daniela Monti

  DOI：10.1016/j.molcatb.2011.12.001

  日期：2012.4

  The substrate preferences of three acylases two wild-type enzymes and an evolved variant obtained by directed evolution - which are prototypical enzymes for glutaryl-7-ACA acylase and cephalosporin C acylase subfamilies, have been investigated. A preliminary screening of enzymes' performances on a large set of substrates has been carried out by a colorimetric assay performed in 96-well plates and by a pH-Star monitoring the hydrolytic activities. Subsequently, kinetic data for selected substrates have been determined, thus elucidating the substrate preference of members of glutaryl-7-ACA acylase vs. cephalosporin C acylase subfamilies. These achievements pave the way to the ability of choosing the best enzyme for the hydrolysis of different compounds of industrial importance. (C) 2011 Elsevier B.V. All rights reserved.
• Adipoyl-6-aminopenicillanic acid is a substrate for deacetoxycephalosporin C synthase (DAOCS)
  作者：Norio Shibata、Matthew D Lloyd、Jack E Baldwin、Christopher J Schofield

  DOI：10.1016/s0960-894x(96)00278-8

  日期：1996.7

  Adipoyl-6-aminopenicillanic acid 5 was incubated with recombinant DAOCS and the resulting cephalosporin isolated. Adipoyl-6-aminopenicillanic acid 5 is approximately 735 times less efficient as a substrate for DAOCS in vitro (as judged by k(cat)/K-m) than penicillin N 1. Copyright (C) 1996 Published by Elsevier Science Ltd
• BALDWIN, JACK E.;ADLINGTON, ROBERT M.;CRABBE, M. JAMES;KNIGHT, GRAHAM;NOM+, TETRAHEDRON,(1987) N 13, 3009-3014
  作者：BALDWIN, JACK E.、ADLINGTON, ROBERT M.、CRABBE, M. JAMES、KNIGHT, GRAHAM、NOM+

  DOI：——

  日期：——