Fmoc-Tyr(Bzl)-Gly-Gly-Phe-Leu-OBzl | 88099-29-0

• 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
• 英文名称: Fmoc-Tyr(Bzl)-Gly-Gly-Phe-Leu-OBzl
• 英文别名: FMOC-Tyr(Bn)-Gly-Gly-Phe-Leu-OBn；benzyl (2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-phenylmethoxyphenyl)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoate
• CAS: 88099-29-0
• 化学式: C₅₇H₅₉N₅O₉
• 分子量: 958.124
• InChiKey: GGMCNUSREGKBEA-HTZDTEJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  71
• 可旋转键数：
  25
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  190
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Fmoc-Tyr(Bzl)-Gly-Gly-Phe-Leu-OBzl 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 24.0h， 以58%的产率得到Leu-enkephalin
  参考文献：
  名称：

  Amino-Protecting Groups Subject to Deblocking under Conditions of Nucleophilic Addition to a Michael Acceptor. Structure−Reactivity Studies and Use of the 2-(tert-Butylsulfonyl)-2-propenyloxycarbonyl (Bspoc) Group

  摘要：

  A new type of amino-protecting group is described in which a Michael acceptor is incorporated into the protectant so that treatment with a nucleophile will trigger deblocking. Comparison of various Michael accepters showed that for several key electron-withdrawing groups, the order of reactivity was C6H5SO2 > Me3CSO2 > COOEt > CsH5SO > C(6)H(4)NO(2-)p. The reactivity of the nucleophile. (e.g., primary and secondary aliphatic amines) followed an order related to both intrinsic basicity and steric effects. beta-Substituents in the Michael acceptor caused significant retardation of the deblocking process. The Bspoc function was chosen for initial elaboration into a practical system for use in peptide synthesis. Bspoc amino acid chlorides were used as coupling agents and silica-tethered secondary amines as deblocking agents. With the latter, deblocking occurs cleanly and no byproducts remain in the organic solvent in which the deblocking is executed.

  DOI：

  10.1021/jo982141d
• 作为产物：
  描述：

  L-苯基丙氨酸叔丁酯 在 氯化亚砜 、 碳酸氢钠 、 4-氨甲基哌啶 、 三氟乙酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 6.33h， 生成 Fmoc-Tyr(Bzl)-Gly-Gly-Phe-Leu-OBzl
  参考文献：
  名称：

  Amino-Protecting Groups Subject to Deblocking under Conditions of Nucleophilic Addition to a Michael Acceptor. Structure−Reactivity Studies and Use of the 2-(tert-Butylsulfonyl)-2-propenyloxycarbonyl (Bspoc) Group

  摘要：

  A new type of amino-protecting group is described in which a Michael acceptor is incorporated into the protectant so that treatment with a nucleophile will trigger deblocking. Comparison of various Michael accepters showed that for several key electron-withdrawing groups, the order of reactivity was C6H5SO2 > Me3CSO2 > COOEt > CsH5SO > C(6)H(4)NO(2-)p. The reactivity of the nucleophile. (e.g., primary and secondary aliphatic amines) followed an order related to both intrinsic basicity and steric effects. beta-Substituents in the Michael acceptor caused significant retardation of the deblocking process. The Bspoc function was chosen for initial elaboration into a practical system for use in peptide synthesis. Bspoc amino acid chlorides were used as coupling agents and silica-tethered secondary amines as deblocking agents. With the latter, deblocking occurs cleanly and no byproducts remain in the organic solvent in which the deblocking is executed.

  DOI：

  10.1021/jo982141d

文献信息

• (Fluoren-9-ylmethoxy)carbonyl (Fmoc) amino acid chlorides. Synthesis, characterization, and application to the rapid synthesis of short peptide segments
  作者：Louis A. Carpino、Beri J. Cohen、Kenton E. Stephens、S. Yahya Sadat-Aalaee、Jien Heh Tien、Denton C. Langridge

  DOI：10.1021/jo00369a042

  日期：1986.9
• Tris(2-aminoethyl)amine as substitute for 4-(aminomethyl)piperidine in the FMOC/polyamine approach to rapid peptide synthesis
  作者：Louis A. Carpino、Dean Sadat-Aalaee、Michael Beyermann

  DOI：10.1021/jo00292a050

  日期：1990.3
• Gopi; Suresh Babu, Journal of the Indian Chemical Society, 1998, vol. 75, # 9, p. 511 - 513
  作者：Gopi、Suresh Babu

  DOI：——

  日期：——
• CARPINO, LOUIS A.;COHEN, BERI J.;LIN, YAO-ZHONG;STEPHENS, KENTON E. (JR);+, J. ORG. CHEM., 55,(1990) N, C. 251-259
  作者：CARPINO, LOUIS A.、COHEN, BERI J.、LIN, YAO-ZHONG、STEPHENS, KENTON E. (JR)、+

  DOI：——

  日期：——
• CARPINO, LOUIS A.;SADAT-AALAEE, DEAN;BEYERNAND, MICHAEL, J. ORG. CHEM., 55,(1990) N, C. 1673-1675
  作者：CARPINO, LOUIS A.、SADAT-AALAEE, DEAN、BEYERNAND, MICHAEL

  DOI：——

  日期：——