Z-Tyr-Gly-Gly-Phe-Leu-NH₂ | 71591-21-4

• 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: Z-Tyr-Gly-Gly-Phe-Leu-NH₂
• 英文别名: Cbz-YGGFL-NH2；Z-Tyr-Gly-Gly-Phe-Leu-NH2；Cbz-Tyr-Gly-Gly-Phe-Leu-NH2；benzyl N-[(2S)-1-[[2-[[2-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-2-oxoethyl]amino]-2-oxoethyl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]carbamate
• CAS: 71591-21-4
• 化学式: C₃₆H₄₄N₆O₈
• 分子量: 688.781
• InChiKey: OCSVZPVBNXYRPU-DTXPUJKBSA-N

物化性质

• 沸点：
  1108.1±65.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：
  218
• 氢给体数：
  7
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Z-Tyr-Gly-Gly-Phe-Leu-NH₂ 在 peptide amidase 12B 、 copper(II) sulfate 、 sodium ascorbate 、 蔗糖 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 72.0h， 生成
  参考文献：
  名称：

  通过计算机工程改造的肽酰胺酶对肽进行酶促可点击的官能化

  摘要：

  摘要通过计算蛋白质工程，通过工程化的生物分子催化剂–酰胺酰胺酶12B实现了定向肽的C末端修饰。该工程化酶在使用丙-2-炔-1-胺（PYA）或丙-2-烯-1-胺（PEA）作为亲核试剂的阿片肽的C末端修饰中显示出巨大的潜力。各种阿片肽可以很容易地以温和和选择性的方式在C末端链上以高产量官能化。值得注意的是，带有炔基部分的修饰的阿片样肽可以通过公认的点击反应进一步功能化。

  DOI：

  10.1016/j.cclet.2018.03.033
• 作为产物：
  描述：

  Cbz-L-Phe-L-Leu-NH2 在 papain thio-2-hydroxyethylene 作用下， 以 甲醇 、 水 为溶剂， 反应 9.0h， 生成 Z-Tyr-Gly-Gly-Phe-Leu-NH₂
  参考文献：
  名称：

  木瓜蛋白酶催化的肽合成：酰胺酶活性的控制和异常氨基酸的引入

  摘要：

  已经开发了木瓜蛋白酶催化的合成含有D-氨基酸的肽和可控制该酶的酰胺酶活性的衍生物的方法。

  DOI：

  10.1039/c39870000533

文献信息

• Enzymes in organic synthesis: use of subtilisin and a highly stable mutant derived from multiple site-specific mutations
  作者：Chi Huey Wong、S. T. Chen、William J. Hennen、Jeffrey A. Bibbs、Y. F. Wang、Jennifer L. C. Liu、Michael W. Pantoliano、Marc Whitlow、Philip N. Bryan

  DOI：10.1021/ja00159a006

  日期：1990.1

  wild-type enzyme to organic synthesis has been demonstrated in the regioselective acylation of nucleosides in anhydrous dimethylformamide (with 65-100% regioselectivity at the 5'-position), in the enantioselective hydrolysis of N-protected and unprotected common and uncommon amino acid esters inmore » water (with 85-98% enantioselectivity for the L-isomer), and in the synthesis of di- and oligopeptides

  发现通过六个位点特异性突变（Met50Phe、Gly169Ala、Asn76Asp、Gln206Cys、Tyr2l7Lys 和 Asn2l8Ser）衍生自枯草杆菌蛋白酶 BPN' 的枯草杆菌蛋白酶突变体（枯草杆菌蛋白酶 8350）在水溶液中比野生溶液中的稳定性高 100 倍在无水二甲基甲酰胺中比野生型稳定 50 倍。使用酯、硫酯和酰胺底物以及过渡态类似物抑制剂 Boc-Ala-Val-Phe-CFsub 3} 的动力学研究表明，野生型和突变型酶具有非常相似的特异性和催化作用特性。野生型酶的抑制常数 (Ki = 5.0 mu}M) 是突变酶 (Ki = 1.1 mu}M) 的约 5 倍，表明突变酶与反应过渡态的结合比野生型酶。该结果与观察到的相应酯和酰胺底物的速率常数一致；即，突变体的 ksub cat}/Ksub m} 值大于野生型酶的值。突变酶和野生型酶在有机合成中的应用已在无
• Peptide synthesis mediated by immobilized and viable baker's yeast in reverse micelles: synthesis of leucine enkephalin analogues
  作者：N. W. Fadnavis、A. Deshpande、S. Chauhan、U. T. Bhalerao

  DOI：10.1039/c39900001548

  日期：——

  Cells of baker's yeast (Saccharomyces cerevisiaeNCIM 3305) immobilized in calcium alginate beads are found to be viable in reverse micelles of bis(2-ethylhexyl)sulphosuccinate sodium salt 1 in iso-octane for days and were used for the first time for peptide synthesis (in aerosol OT reverse micelles) using hydrophobic substrates.

  发现固定在海藻酸钙珠粒中的面包酵母（Saccharomyces cerevisiae NCIM 3305）细胞在异辛烷中的双（2-乙基己基）磺基琥珀酸钠盐1的反胶束中可存活数天，并首次用于肽合成（在气溶胶OT反胶束中）使用疏水性底物。
• Encapsulation of Biologicals within Silicate, Siloxane, and Hybrid Sol−Gel Polymers:  An Efficient and Generic Approach
  作者：Iqbal Gill、Antonio Ballesteros

  DOI：10.1021/ja9814568

  日期：1998.9.1

  The sol-gel encapsulation of labile biological materials with catalytic and recognition functions within robust polymer matrices remains a challenging task, despite the considerable research that has been focused on this field. Herein, we describe a new class of precursors, based around polyol silicates and polyol siloxanes, especially those derived from glycerol, that addresses problems faced with traditional bioencapsulation protocols. Poly(glyceryl silicate) (PGS) was prepared and employed for sol-gel bioentrapment, in an approach distinguished by a high biocompatibility and mild encapsulation conditions, and which enables the reproducible and efficient confinement of proteins and cells inside silica. The methodology was extended to metallosilicate, alkylsiloxane, functionalized siloxane, and composite sol-gels, thereby allowing the fabrication of a physicochemically diverse range of bio-doped polymers. The hybrid materials display activities approaching those of the free biologicals, together with the high stabilities and robustness that characterize sol-gel bioceramics. Indeed, the bioencapsulates performed better than those fabricated from tetramethoxysilane, poly (methyl silicate) or alcohol-free poly(silicic acid), even when the latter were doped with glycerol. The activity enhancements appear to derive at least in part from the unusual microstructure of PGS sol-gels, in particular their high porosity, although the underlying mechanisms are unclear. Differences in precursor hydrolysis/condensation, development of gel structure, biological-matrix interactions, precursor toxicity, and pore collapse probably all contribute to the observed efficiency of the PGS materials. The performances of the encapsulates are compared with conventional sol-biogels and other immobilizates, in representative biocatalyst, biosensor, and biodiagnostic applications.
• Gill, Iqbal; Vulfson, Evgeny N., Journal of the Chemical Society. Perkin transactions I, 1992, # 6, p. 667 - 668
  作者：Gill, Iqbal、Vulfson, Evgeny N.

  DOI：——

  日期：——
• Peptide segment synthesis catalyzed by the semisynthetic enzyme thiolsubtilisin
  作者：T. Nakatsuka、T. Sasaki、E. T. Kaiser

  DOI：10.1021/ja00246a064

  日期：1987.6