7β-(4-Carboxybutanamido)desacetoxycephalosporanic acid | 60758-77-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 7β-(4-Carboxybutanamido)desacetoxycephalosporanic acid
• 英文别名: 7-(glutarylamino)desacetoxycephalosporanic acid；(6R,7R)-7-[(4-carboxy-1-oxobutyl)amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid；(6R,7R)-7-(4-carboxybutanoylamino)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 60758-77-2
• 化学式: C₁₃H₁₆N₂O₆S
• 分子量: 328.346
• InChiKey: KFAZOAVBYQAACA-BXKDBHETSA-N

物化性质

• 沸点：
  778.5±60.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  7β-(4-Carboxybutanamido)desacetoxycephalosporanic acid 在 sodium hydroxide 、 glutaryl-7-aminocephalosporanic acid acylase 作用下， 以 水 为溶剂， 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：

  谷氨酰酰化酶：单反应酶还是多功能对映选择性生物催化剂？

  摘要：

  用工业戊二酰-7-氨基头孢烷酸酰基转移酶（GA）已观察到跨越常规β-内酰胺衍生物的显着广泛的底物特异性。该酶具有显着的对映选择性酰胺酶和甚至酯酶活性，并具有S-对映异构体的立体偏好。通过溶剂萃取，避免在反应后处理过程中避免色谱或蒸馏，可以轻松地将具有不同物理化学性质的产物与未反应的试剂分离。

  DOI：

  10.1002/adsc.200303013
• 作为产物：
  描述：

  (2S,5R,6R)-1-aza-3,3'-dimethyl-6-(4-carboxybutanamido)-7-oxo-4-thiabicyclo<3.2.0>heptane-2-carboxylic acid 以 水 为溶剂， 反应 2.0h， 生成 7β-(4-Carboxybutanamido)desacetoxycephalosporanic 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：

  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

  DOI：

  10.1016/s0040-4020(01)86840-x

文献信息

• Enzymatic ring expansion of penicillins to cephalosporins: side chain specificity
  作者：Jack E. Baldwin、Robert M. Adlington、Janice B. Coates、M. James C. Crabbe、John W. Keeping、Graham C. Knight、Takashi Nomoto、Christopher J. Schofield、Hong-Hoi Ting

  DOI：10.1039/c39870000374

  日期：——

  Structural variants on the acylamino-side chains of penicillins as substrates for the ring expansion enzyme from Cephalosporium acremonium CO728 show that a six carbon chain terminating in a carboxy group permits efficient conversion into cephems with the exception of δ-(L-α-aminoadipoly)[5-(5S)-amino-5-carboxypentanoyl].

  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]。
• 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.
• Shibuya, Yuzo; Matsumoto, Kunio; Fuji, Tadashiro, Agricultural and Biological Chemistry, 1981, vol. 45, # 7, p. 1561 - 1568
  作者：Shibuya, Yuzo、Matsumoto, Kunio、Fuji, Tadashiro

  DOI：——

  日期：——
• 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：——