Boc-L-半胱氨酸苄酯-Osu | 3401-33-0

• 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
• 中文名称: Boc-L-半胱氨酸苄酯-Osu
• 中文别名: BOC-S-苄基-L-半胱氨酸琥珀酰亚胺酯；BOC-S-苄基-L-半胱氨酸琥珀酰亚胺基酯
• 英文名称: Boc-Cys(Bzl)-OSu
• 英文别名: (2,5-dioxopyrrolidin-1-yl) (2R)-3-benzylsulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 3401-33-0
• 化学式: C₁₉H₂₄N₂O₆S
• 分子量: 408.475
• InChiKey: TVSSLLYGMLXNIC-AWEZNQCLSA-N

物化性质

• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 储存条件：
  存储条件：室温、密封、干燥

反应信息

• 作为反应物：
  描述：

  Boc-L-半胱氨酸苄酯-Osu 在 N-甲基吗啉 、 盐酸 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 N-benzyloxycarbonyl-α-benzyl-δ-(L-α-aminoadipoyl)-S-benzyl-L-cysteinyl-D-valine benzyl ester
  参考文献：
  名称：

  Liberek, Bogdan; Kasprzykowska, Regina; Wisniewski, Kazimierz, Collection of Czechoslovak Chemical Communications, 1988, vol. 53, # 11B, p. 2857 - 2862

  摘要：

  DOI：
• 作为产物：
  描述：

  Boc-S-苄基-L-半光氨酸 、 N-(1,2,2,2-四氯乙氧基羰基氧)琥珀酰亚胺 在 N-甲基吗啉 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 以61%的产率得到Boc-L-半胱氨酸苄酯-Osu
  参考文献：
  名称：

  Novel preparation of N-protected amino acid active esters using 1,2,2,2-tetrachloroethyl carbonates

  摘要：

  DOI：

  10.1021/jo00388a005

文献信息

• Production of Atosiban’s Key Intermediate Pentapeptide: Synthetic Approaches to the Development of a Peptide Synthesis with Less Racemization and Simplifier Purification Process
  作者：Chunying Ma、Yixuan Zheng、Jinwei Liu、Xiaobao Li、Wenhua Feng

  DOI：10.3390/molecules27061920

  日期：——

  stepwise lengthening of the chain according to the repetitive N,O-bis(trimethylsilyl)acetamide/N-hydroxysuccinimide ester (BSA/NHS) strategy. This synthetic route required no chromatography purification and can be readily performed, yielding a highly pure pentapeptide compound.

  阿托西班的关键中间体 NH 2 -Ile-Thr(Bzl)-Asn-Cys(Bzl)-Pro-COOH 是由N -Boc- S -Bzl-半胱氨酸根据重复的N逐步延长链制备的，O-双（三甲基甲硅烷基）乙酰胺/ N-羟基琥珀酰亚胺酯（BSA/NHS）策略。该合成路线不需要色谱纯化并且可以很容易地进行，产生高纯度的五肽化合物。
• Hypocalcaemic peptides and processes for their manufacture
  申请人：Ciba-Geigy Corporation

  公开号：US03956260A1

  公开（公告）日：1976-05-11

  Synthetic hypocalcaemic dotriacontapeptide of the formula H-Cys-Ser-Asn-Leu-Ser--Thr-Cys-Val-Leu-Ser-Ala-Tyr-Try-Arg-Asn-Leu-Asn-Asn- Phe-His-Arg-Phe-Ser-Gly-Met-Gly-Phe-Gly-Pro-Glu-Thr-Pro-OH I and analogues and derivatives, salts and complexes thereof and process for their manufacture.

  合成低钙血性三十二肽的公式为H-Cys-Ser-Asn-Leu-Ser-Thr-Cys-Val-Leu-Ser-Ala-Tyr-Try-Arg-Asn-Leu-Asn-Asn-Phe-His-Arg-Phe-Ser-Gly-Met-Gly-Phe-Gly-Pro-Glu-Thr-Pro-OH I及其类似物和衍生物，盐和配合物及其制备方法。
• Anagnostaras; Cordopatis; Theodoropoulos, European Journal of Medicinal Chemistry, 1981, vol. 16, # 2, p. 171 - 173
  作者：Anagnostaras、Cordopatis、Theodoropoulos

  DOI：——

  日期：——
• [5-(N4,N4-Dimethylasparagine),8-lysine]vasopressin: the first 5-position neurohypophyseal hormone analog to retain significant antidiuretic potency
  作者：Clark W. Smith、Roderich Walter、George Stavropoulos、Dimitrios Theodoropoulos

  DOI：10.1021/jm00176a021

  日期：1980.2

  In the proposed biologically active conformation of vasopressin at the antidiuretic receptor, the side-chain carboxamide group of the 5-position asparaginyl residue has been previously suggested to be the key active element in the hormone for its initiation of the antidiuretic response. [5-(N4,N4-Dimethylasparagine),8-lysine]vasopressin, the analogue in which the hydrogen atoms of the -NH2 portion of the primary carboxamide have been replaced by methyl groups, has been synthesized and found to retain about 3% of the antidiuretic potency of lysine-vasopressin (i.e., 5.5 +/- 0.3 units/mg). This result suggests that the hydrogen atoms of the carboxamide moiety are not essential for antidiuretic activity. In addition, the analogue possesses rat pressor, avian vasodepressor, and rat uterotonic potencies of 2.55 +/- 0.05, 0.39 +/- 0.03, and less than 0.05 units/mg, respectively.
• Effect of changing the COOH-terminal amide group present in the hydrophilic cluster of oxytocin to dimethylamide
  作者：Yuan Fen Ting、Clark W. Smith、Glenn L. Stahl、Roderich Walter、Paul Cordopatis、Dimitrios Theodoropoulos

  DOI：10.1021/jm00180a026

  日期：1980.6

  Oxytocinoic acid dimethylamide was synthesized by stepwise solution techniques as part of an ongoing evaluation of the effects on the biological activity of oxytocin caused by individually changing the groups that comprises the hydrophilic surface of the hormone to more hydrophobic and more bulky groups. The analogue exhibited approximately 3% of the potency of oxytocin in the in vitro uterotonic assay. In addition, it possesses potencies of less than 0.07, less than 0.01, and 0.096 unit/mg in the avian vasodepressor, rat pressor, and rat antidiuretic assays, respectively. In the in vitro uterotonic assay, oxytocinoic acid dimethylamide showed a reduced affinity for the oxytocin receptor, a nonparallel dose-response relationship, and most importantly a reduced intrinsic activity as compared to oxytocin. The results suggest that the replacement of the protons of the primary carboxyamide of Gly9-NH2 of oxytocin by methyl groups displaces the active elements from the orientation for obtaining maximal intrinsic activity in the isolated rat uterus.