N-(p-nitrobenzyloxycarbonyl)-D-α-aminoadipic acid 1-p-nitrobenzyl ester | 74271-82-2

• 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: N-(p-nitrobenzyloxycarbonyl)-D-α-aminoadipic acid 1-p-nitrobenzyl ester
• 英文别名: 5R-5-p-nitrobenzyloxycarbonylamino-5-p-nitrobenzyloxycarbonylpentanoic acid；(5R)-6-[(4-nitrophenyl)methoxy]-5-[(4-nitrophenyl)methoxycarbonylamino]-6-oxohexanoic acid
• CAS: 74271-82-2
• 化学式: C₂₁H₂₁N₃O₁₀
• 分子量: 475.412
• InChiKey: BSQROHSOIULBLT-GOSISDBHSA-N

物化性质

• 熔点：
  110 °C
• 沸点：
  722.7±60.0 °C(Predicted)
• 密度：
  1.427±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  34.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  188.21
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (5R)-6t-amino-3,3,6c-trimethyl-7-oxo-(5rH)-4-thia-1-aza-bicyclo[3.2.0]heptane-2c-carboxylic acid benzyl ester 、 N-(p-nitrobenzyloxycarbonyl)-D-α-aminoadipic acid 1-p-nitrobenzyl ester 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以52%的产率得到benzyl (2S,5R,6R)-3,3,6-trimethyl-6-[[(5R)-6-[(4-nitrophenyl)methoxy]-5-[(4-nitrophenyl)methoxycarbonylamino]-6-oxohexanoyl]amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
  参考文献：
  名称：

  Contrasting fates for 6-α-methylpenicillin N upon oxidation by deacetoxycephalosporin C synthase (DAOCS) and deacetoxy/deacetylcephalosporin C synthase (DAOC/DACS)

  摘要：

  6-alpha -Methylpenicillin N was synthesised via known routes from 6-aminopenicillanic acid, and tested as a substrate for recombinant DAOCS and DAOC/DACS. Incubation with DAOCS resulted in conversion of 2-oxoglutarate without oxidation of the penicillin substrate ('uncoupled turnover'). Incubation with DAOC/DACS resulted in oxidation to the cephem aldehyde. This is the first example of substrate-induced 'uncoupled turnover', which has been proposed to be an editing mechanism for these enzymes. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00470-x
• 作为产物：
  描述：

  (2R)-2-[(4-nitrophenyl)methoxycarbonylamino]hexanedioic acid 、 对硝基溴化苄 以23%的产率得到
  参考文献：
  名称：

  HUFFMAN, GEORGE W., ORG. PREP. AND PROCED. INT., 20,(1988) N 5, C. 497-503

  摘要：

  DOI：

文献信息

• The enzymatic conversion of exomethylene cephalosporin c into deacetyl cephalosporin c and the role of molecular oxygen in cephalosporin c biosynthesis
  作者：Jack E. Baldwin、Robert M. Adlington、Nicholas P. Crouch、Christopher J. Schofield

  DOI：10.1016/s0040-4020(01)85852-x

  日期：1988.1

  Cell free extracts from containing deaoetoxy/-deacetyl cephalosporin C Synthetase activities have been shown to convert Exomethylene cephalosporin C directly to deacetyl cephalosporin C. Labelling experiments in the presence of 13O2, indicated the source of the 3-methylene-oxygen of the latter was dioxygen.1

  已显示，含有脱氧乙氧基/-去乙酰头孢菌素C合成酶活性的无细胞提取物可将Exomethyl头孢菌素C直接转化为脱乙酰头孢菌素C。在13 O 2存在下的标记实验表明后者的3-亚甲基氧的来源是双氧。1个
• BALDWIN, JACK E.;ADLINGTON, ROBERT M.;CROUCH, NICHOLAS P.;SCHOFIELD, CHRI+, TETRAHEDRON, 44,(1988) N 2, 643-650
  作者：BALDWIN, JACK E.、ADLINGTON, ROBERT M.、CROUCH, NICHOLAS P.、SCHOFIELD, CHRI+

  DOI：——

  日期：——