S-benzyl-N-carbobenzoxy-L-cysteine p-nitrophenyl ester | 3401-37-4

• 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: S-benzyl-N-carbobenzoxy-L-cysteine p-nitrophenyl ester
• 英文别名: α-carbobenzoxy-L-benzylcysteine p-nitrophenyl ester；p-Nitrophenylester of benzyloxycarbonyl-S-benzylcysteine；Z-L-Cys(Bzl)-ONp；L-ZCys(Bzl)ONp；Z-Cys(Bzl)-ONp；S-benzyl-N-benzyloxycarbonyl-L-cysteine-(4-nitro-phenyl ester)；(4-nitrophenyl) (2R)-3-benzylsulfanyl-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 3401-37-4
• 化学式: C₂₄H₂₂N₂O₆S
• 分子量: 466.514
• InChiKey: LQPKVCBYFUURJM-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  136
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• WGK Germany：
  3
• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  S-benzyl-N-carbobenzoxy-L-cysteine p-nitrophenyl ester 在 N-decanoyl-L-histidine methyl ester 十六烷基三甲基溴化铵 作用下， 以 水 为溶剂， 生成 N-苄氧羰基-S-苄基-L-半胱氨酸
  参考文献：
  名称：

  Ihara, Yasuji; Hosako, Reiko; Nango, Mamoru, Journal of the Chemical Society. Perkin transactions II, 1983, p. 5 - 10

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-2-Amino-3-benzylsulfanyl-propionic acid 4-nitro-phenyl ester; hydrochloride 在 吡啶 作用下， 以 甲苯 、 苯 为溶剂， 生成 S-benzyl-N-carbobenzoxy-L-cysteine p-nitrophenyl ester
  参考文献：
  名称：

  Überneue ，Kristalline N-羰基氨基氨基脲酸酯

  摘要：

  模具Darstellung冯kristallinen ñ -羰基aminosäureesternmehrfunktionellerAminosäurenUND IHREAnwendungsmöglichkeiten在德Peptidchemie wird beschrieben。

  DOI：

  10.1002/cber.19671001020

文献信息

• Synthesis of activated esters of N-protected amino-acids
  作者：Y. Wolman、D. Ladkany、Max Frankel

  DOI：10.1039/j39670000689

  日期：——

  A simplified method for the synthesis of activated esters of N-protected amino-acids is described. The synthesis proceeds through the aminolysis of various active esters of t-butyl or benzyl carbonate, and the leaving group displaced in this process becomes reincorporated by the additon of dicyclohexylcarbodi-imide to the reaction mixture, to give the desired compound.

  描述了一种用于合成N-保护的氨基酸的活化酯的简化方法。合成通过碳酸叔丁酯或碳酸苄酯的各种活性酯的氨解进行，并且在该过程中置换的离去基团通过将二环己基碳二亚胺添加到反应混合物中而重新结合，从而得到所需化合物。
• A Proposal for Using Mild Bases in the Preparation of Optically Pure Peptides
  作者：Shumpei Sakakibara、Masumi Itoh

  DOI：10.1246/bcsj.40.656

  日期：1967.3

  p-nitrophenyl ester was studied with various tertiary amines; N, N-dialkylglycine esters and N-ethylmorpholine were found to induce less racemization than triethylamine. Furthermore, these mild bases were strong enough in many cases to liberate free amino acid or peptide esters from their salts. It was also confirmed that a mixture of an amino acid or peptide ester salt and such a mild base could be used in the

  用各种叔胺研究了 N-羧基苯甲氧基-S-苄基-L-半胱氨酸对硝基苯酯的碱催化外消旋化反应；发现 N, N-二烷基甘氨酸酯和 N-乙基吗啉比三乙胺诱导更少的外消旋化。此外，这些弱碱在许多情况下足够强以从它们的盐中释放游离氨基酸或肽酯。也证实了氨基酸或肽酯盐和这种弱碱的混合物可以代替先前制备的游离酯用于肽合成，并且在与酰基氨基酸的偶联反应过程中几乎没有观察到外消旋化活性酯。Anderson 的外消旋化试验也是通过混合酸酐程序用这些弱碱代替三乙胺进行的；发现弱碱在光学纯度方面产生更好的结果。
• Neue Methoden zur Herstellung von Carbonsäure-arylestern. Über aktivierte Ester VIII
  作者：B. Iselin、W. Rittel、P. Sieber、R. Schwyzer

  DOI：10.1002/hlca.19570400216

  日期：——

  Two new methods for preparing carboxylic acid aryl esters are presented. They consist in reacting the carboxylic acid with (a) aryl sulfites or (b) aryl phosphites in the presence of pyridine. A possible mechanism of the sulfite method is discussed.

  提出了两种制备羧酸芳基酯的新方法。它们在于使羧酸与（a）亚硫酸芳基酯或（b）亚磷酸芳基酯在吡啶存在下反应。讨论了亚硫酸盐法的可能机理。
• Oxytocin analogues with inhibitory properties, containing in position 2 a hydrophobic amino acid of D-configuration
  作者：Michal Lebl、Tomislav Barth、Linda Servítová、Jiřina Slaninová、Karel Jošt

  DOI：10.1135/cccc19850132

  日期：——

  Ten analogues derived from oxytocin, deamino-oxytocin and deamino-carba-oxytocin were prepared which contained a D-amino acid in the position 2 of the parent system. The following D-amino acids were introduced: tyrosine, phenylalanine, p-methylphenylalanine, p-ethylphenylalanine and O-ethyltyrosine. Combination of two structural features which alone lead to strong inhibitors (a suitable D-amino acid in position 2 and a penicillamine moiety in position 1) did not enhance the inhibitory effect. Compounds containing D-tyrosine are weak agonists in the uterotonic assay; in case of 1-carba-analogues they can be converted into sulfoxides with low inhibitory activity. Analogues with D-phenylalanine substituted in the para-position are the most potent antagonists of the uterotonic effect of oxytocin (pA₂ = 8.73) in vitro.

  从催产素、去氨基催产素和去氨基卡巴催产素中制备了十种类似物，其中在母体系统的位置2含有D-氨基酸。引入了以下D-氨基酸：酪氨酸、苯丙氨酸、对甲基苯丙氨酸、对乙基苯丙氨酸和O-乙基酪氨酸。单独引起强抑制剂作用的两种结构特征的组合（位置2中适当的D-氨基酸和位置1中的青霉胺基团）并未增强抑制作用。含有D-酪氨酸的化合物在子宫收缩实验中是弱激动剂；在1-卡巴类似物的情况下，它们可以转化为具有低抑制活性的亚砜。在对位替代D-苯丙氨酸的类似物中，它们是催产素子宫效应最有效的拮抗剂（pA2 = 8.73）体外。
• Ribonuclease T₁Peptides. I. Synthesis of a Protected<i>N</i>-Terminal Undecapeptide Containing Asparagine Residue in Third Position
  作者：Motonori Ohno、Tetsuo Kato、Nobuo Mitsuyasu、Michinori Waki、Satoru Makisumi、Nobuo Izumiya

  DOI：10.1246/bcsj.40.204

  日期：1967.1

  A protected undecapeptide containing the possible N-terminal sequence of ribonuclease T1, namely benzyloxycarbonyl-l-alanyl-S-benzyl-l-cysteinyl-l-asparaginyl-l-tyrosyl-l-threonyl-S-benzyl-l-cysteinyl-glycyl-l-seryl-l-asparaginyl-S-benzyl-l-cysteinyl-l-tyrosine ethyl ester (XXI), was synthesized by coupling of benzyloxycarbonyl-alanyl-S-benzylcysteinyl-asparaginyl-tyrosine azide with heptapeptide ester, threonyl-S-benzylcysteinyl-glycyl-seryl-asparaginyl-S-benzylcysteinyl-tyrosine ester, which is derived from p-methoxybenzyloxycarbonyl-heptapeptide ester by the action of trifluoroacetic acid. The optical homogeneity of the protected undecapeptide (XXI) was established by deblocking of XXI and subsequently digesting the resulting free undecapeptide with leucine aminopeptidase.

  由对甲氧基苄氧羰基七肽酯与苏氨酰-S-苄基-天冬氨酰-甘氨酰-丝氨酰-天冬氨酰-S-苄基-天冬氨酰-酪氨酸酯偶联合成。通过解锁 XXI 并用亮氨酸氨肽酶消化游离出的后十肽，确定了受保护的后十肽（XXI）的光学均匀性。