Cbz-Tyr-Gly-Gly-Phe-Leu-OH | 80645-37-0

• 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: Cbz-Tyr-Gly-Gly-Phe-Leu-OH
• 英文别名: (2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-3-(4-hydroxyphenyl)-2-(phenylmethoxycarbonylamino)propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoic acid
• CAS: 80645-37-0
• 化学式: C₃₆H₄₃N₅O₉
• 分子量: 689.766
• InChiKey: SAZLRMUOUMYWRG-DTXPUJKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  50
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  212
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Cbz-Tyr-Gly-Gly-Phe-Leu-OH 生成 (S)-2-[(S)-2-(2-{2-[(S)-2-Benzyloxycarbonylamino-3-(4-hydroxy-3,5-diiodo-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid
  参考文献：
  名称：

  First aromatic electrophilic iodination reaction on the solid-phase: Iodination of bioactive peptides

  摘要：

  Direct iodination of Tyr residues of peptides anchored on solid supports was accomplished, for the first time, by aromatic electrophilic attack of iodonium ions provided by the IPy2BF4 reagent. Compatibility studies of the iodination with routine solid-phase synthesis protocols are reported. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01604-9
• 作为产物：
  描述：

  Z-Tyr-Gly-Gly-OEt 在 sodium hydroxide 、 calcium acetate 、 三氯化铁 、 三乙胺 、 thermolysin 作用下， 以 1,4-二氧六环 、 吡啶 、 2-甲基-2-丁醇 、 水 为溶剂， 反应 96.0h， 生成 Cbz-Tyr-Gly-Gly-Phe-Leu-OH
  参考文献：
  名称：

  有机溶剂中N保护的亮脑啡肽和一些寡肽的酶促合成

  摘要：

  研究了生物活性五肽，N-保护的亮脑啡肽和其他一些寡肽在有机溶剂中的酶促合成。通过使用外消旋底物检查酶促反应的立体选择性。比较了不同的酶，溶剂系统和保护基。讨论了必需水的重要性。在所有酶促反应过程中，酪氨酸的侧链均未得到保护。在混合溶剂或有机溶剂中，通过木瓜蛋白酶和α-胰凝乳蛋白酶将P-DL-AlaOY（P = Z或Boc，YH或Me）和P-DL-TyrOEt与GlyNHNHPh偶联，以获得所需的光学纯产物PL-AlaGlyNHNHPh和PL-TyrGlyNHNHPh分别以良好的收率。两个甜味剂前体，ZAspXaaOR（XaaOR = PheOMe或AlaOcHex）通过嗜热菌中合成叔对戊醇和一些反应条件进行了优化以获得最佳收率。使用α-胰凝乳蛋白酶和嗜热菌蛋白酶作为催化剂，在二氯甲烷和叔戊醇中，研究了N-保护的亮脑啡肽ZTyrGlyGlyPheLeuOH的完全酶促合成。

  DOI：

  10.1016/s0040-4020(98)00737-6

文献信息

• Carbohydrate Protease Conjugates: Stabilized Proteases for Peptide Synthesis
  作者：Charles A. Wartchow、Peng Wang、Mark D. Bednarski、Matthew R. Callstrom

  DOI：10.1021/jo00112a049

  日期：1995.4

  The synthesis of oligopeptides using stable carbohydrate protease conjugates (CPCs) was examined in acetonitrile solvent systems. CPC[alpha-chymotrypsin] was used for the preparation of peptides containing histidine, phenylalanine, tyrosine, and tryptophan in the P-1 position in 60-93% yield. The CPC[alpha-chymotrypsin]-catalyzed synthesis of octamer Z-Gly-Gly-Phe-Gly-Gly-Phe-Gly-Gly-OEt from Z-Gly-Gly-Phe-Gly-Gly-Phe-OMe was achieved in 71% yield demonstrating that synthesis was the dominant kinetic process relative to amide hydrolysis. CPC[papain] was used to synthesize peptides containing both hydrophilic and hydrophobic amino acids. The Pt specificity of papain for aromatic residues was utilized for the 2 + 3 coupling of Z-Tyr-Gly-OMe to H2N-Gly-Phe-Leu-OH to generate the leucine enkephalin derivative in 79% yield. Although papain is nonspecific for the hydrolysis of N-benzyloxycarbonyl amino acid methyl esters in aqueous solution, the rates of synthesis for these derivitives with nucleophile leucine tert-butyl ester differed by nearly 2 orders of magnitude. CPC[thermolysin] was used to prepare the aspartame precursor Z-Asp-Phe-OMe in 90% yield. The increased stability of CPCs prepared from periodate-modified poly(2-methacrylamido-2-deoxy-D-glucose), poly(2-methacrylamido-2-deoxy-D-galactcose) and poly(5-methacrylamido-5-deoxy-D-ribose), carbohydrate materials designed to increase the aldehyde concentration in aqueous solution, suggests that the stability of CPCs is directly related to the aldehyde concentration of the carbohydrate material. Periodate oxidation of poly(2-methacrylamido-2-deoxy-D-glucose) followed by covalent attachment to a-chymotrypsin gave a CPC with catalytic activity in potassium phosphate buffer at 90 degrees C for 2 h.
• 3-hydroxypropionitrile: A new reagent for carboxyl protection in peptide synthesis
  作者：P.K. Misra、S.A.N. Hashmi、W. Haq、S.B. Katti

  DOI：10.1016/s0040-4039(00)99443-7

  日期：1989.1
• MISRA, P. K.;HASHMI, S. A. N.;HAQ, W.;KATTI, S. B., TETRAHEDRON LETT., 30,(1989) N7, C. 3569-3572
  作者：MISRA, P. K.、HASHMI, S. A. N.、HAQ, W.、KATTI, S. B.

  DOI：——

  日期：——
• First aromatic electrophilic iodination reaction on the solid-phase: Iodination of bioactive peptides
  作者：Gemma Arsequell、Gemma Espuña、Gregorio Valencia、José Barluenga、Raquel Pérez Carlón、JoséM. González

  DOI：10.1016/s0040-4039(98)01604-9

  日期：1998.10

  Direct iodination of Tyr residues of peptides anchored on solid supports was accomplished, for the first time, by aromatic electrophilic attack of iodonium ions provided by the IPy2BF4 reagent. Compatibility studies of the iodination with routine solid-phase synthesis protocols are reported. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• Enzymatic syntheses of N-protected Leu-enkephalin and some oligopeptides in organic solvents
  作者：Yun-Hua Ye、Gui-Ling Tian、Guo-Wen Xing、Dong-Cheng Dai、Gang Chen、Chong-Xi Li

  DOI：10.1016/s0040-4020(98)00737-6

  日期：1998.10

  Enzymatic syntheses of bioacitive pentapeptide, N-protected Leu-enkephalin and some other oligopeptides in organic solvents were studied. The stereoselectivity of the enzymatic reaction was examined by using racemic substrates. Different enzymes, solvent systems and protecting groups were compared. The importance of the essential water was addressed. The side chain of tyrosine was not protected during

  研究了生物活性五肽，N-保护的亮脑啡肽和其他一些寡肽在有机溶剂中的酶促合成。通过使用外消旋底物检查酶促反应的立体选择性。比较了不同的酶，溶剂系统和保护基。讨论了必需水的重要性。在所有酶促反应过程中，酪氨酸的侧链均未得到保护。在混合溶剂或有机溶剂中，通过木瓜蛋白酶和α-胰凝乳蛋白酶将P-DL-AlaOY（P = Z或Boc，YH或Me）和P-DL-TyrOEt与GlyNHNHPh偶联，以获得所需的光学纯产物PL-AlaGlyNHNHPh和PL-TyrGlyNHNHPh分别以良好的收率。两个甜味剂前体，ZAspXaaOR（XaaOR = PheOMe或AlaOcHex）通过嗜热菌中合成叔对戊醇和一些反应条件进行了优化以获得最佳收率。使用α-胰凝乳蛋白酶和嗜热菌蛋白酶作为催化剂，在二氯甲烷和叔戊醇中，研究了N-保护的亮脑啡肽ZTyrGlyGlyPheLeuOH的完全酶促合成。