ZL-精氨酸N-羟基琥珀酰亚胺酯 | 132160-73-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: ZL-精氨酸N-羟基琥珀酰亚胺酯
• 英文名称: Z-Arg(Z2)-OSu
• 英文别名: Tris(benzyloxycarbonyl)-L-arginin-N-hydroxy-succinimidester；Z-Arg(Z)2-Osu；(2,5-dioxopyrrolidin-1-yl) (2S)-5-[bis(phenylmethoxycarbonylamino)methylideneamino]-2-(phenylmethoxycarbonylamino)pentanoate
• CAS: 132160-73-7
• 化学式: C₃₄H₃₅N₅O₁₀
• 分子量: 673.679
• InChiKey: VXTIDXYCZXQJKB-MHZLTWQESA-N

物化性质

• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  49
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  191
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  ZL-精氨酸N-羟基琥珀酰亚胺酯 在 palladium on activated charcoal sodium hydroxide 、 N-羟基丁二酰亚胺 、 hydroxyoxobenzotriazine 、 氢溴酸 、 氢气 、 potassium hydrogencarbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 H-Arg(HBr)-Leu-Leu-Gln-Gly-Leu-Val-NH2
  参考文献：
  名称：

  Zur Totalsynthese von Human-Sekretin

  摘要：

  The synthesis of the heptacosapeptide amide with the primary structure of Human-secretin is described. For this purpose 7 fragments were designed, i.e. H-Gly-Leu-Val-NH2 [25-27b], Z-Arg(Z2)-Leu-Leu-Gln-OH [21-24], Z-Arg(Z2)-Leu-Gln-OH[18-20], Z-Arg(Z2)-Glu(OtBu)-Gly-Ala-OH [14-17], Z-Arg(Z2)-Leu-OH [12-13], Z-Thr(tBu)-Ser(tBu)-Glu(OtBu)-Leu-Ser(tBu)-OH [7-11], Adoc-His(Adoc)-Ser(tBu)-Asp(OtBu)-Gly-Thr(tBu)-Phe-OH [1-6]; these fragments were consequently assembled to the overall protected total sequence using the Wunsch/Weygand-method with dicyclohexylcarbodiimide. After deprotection by exposure to trifluoroacetic acid in presence of 1,2-ethanedithiol and water as scavenger, the isolated crude product was purified by column chromatography on CM-Sepharose, fast flow. This synthetized Human-secretin showed the full biological activity in comparison to Porcine-secretin.

  DOI：

  10.1007/bf00819525
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 N_α,N_δ,N_ω-tri-CBZ-L-arginine 在 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 ZL-精氨酸N-羟基琥珀酰亚胺酯
  参考文献：
  名称：

  Direct PCR amplification of various modified DNAs having amino acids: Convenient preparation of DNA libraries with high-potential activities for in vitro selection

  摘要：

  We synthesized modified 2'-deoxyuridine triphosphates bearing amino acids at the C5 position and investigated their substrate properties for KOD Dash DNA polymerase during polymerase chain reaction (PCR). PCR using C5-modified dUTP having an amino acyl group (arginyl, histidyl, lysyl, phenylalanyl, tryptophanyl, leucyl, prolyl, glutaminyl, seryl, O-benzyl seryl or threonyl group) gave the corresponding full-length PCR products in good yield. Although dUTP analogues bearing aspartyl, glutamyl or cysteinyl were found to be poor substrates for PCR catalyzed by KOD Dash DNA polymerase, optimization of the reaction conditions resulted in substantial generation of full-length product. In the case of reaction using dUTP analogue having a cysteinyl group, addition of a reducing agent improved the reaction yield. Thus, PCRs using KOD Dash DNA polymerase together with amino acyl dUTP provide convenient and efficient preparation of various modified DNA libraries with potential protein-like activities. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.030

文献信息

• Design and synthesis of peptide derivatives of a 3-deoxy-D-manno-2-octulosonic acid (KDO) analog as novel antibacterial agents acting upon lipopolysaccharide biosynthesis
  作者：Alf Claesson、Anita M. Jansson、Brian G. Pring、Stephen M. Hammond、Bertil Ekstroem

  DOI：10.1021/jm00395a022

  日期：1987.12

  cytidylyltransferase, attempts were made to design derivatives that would act as antibacterials against Gram-negative bacteria by inhibiting lipopolysaccharide biosynthesis. Compound 3 and the derivatives 15 and 16 containing an additional amino acid were not lethal to bacteria. However, compounds 17-22, which contain a N-terminally linked dipeptide, exhibited good antibacterial activity in vitro on testing against

  基于以下认识，氨基酸3（8-氨基-2,6-脱水-3,8-二脱氧-D-甘油-D-talo-辛酸）是有效的3-脱氧-甘露聚糖-抑制剂试图通过设计八辛酸胞苷基转移酶来设计衍生物，该衍生物通过抑制脂多糖的生物合成来作为革兰氏阴性菌的抗菌剂。化合物3以及含有额外氨基酸的衍生物15和16对细菌没有致死性。但是，含有N末端连接的二肽的化合物17-22在体外测试对革兰氏阴性细菌大肠杆菌和鼠伤寒沙门氏菌的菌株时表现出良好的抗菌活性。它们对革兰氏阳性细菌如金黄色葡萄球菌没有活性。
• Moroder, L.; Goehring, W.; Thamm, P., Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1982, vol. 37, # 6, p. 772 - 780
  作者：Moroder, L.、Goehring, W.、Thamm, P.、Wuensch, E.、Tatemoto, K.、et al.

  DOI：——

  日期：——
• Zur Synthese von Motilin, I. Darstellung der Sequenzen 9-22 von [13-Norleucin]motilin und [13-Leucin] motilin
  作者：Erich WÜNSCH、Gerhard WENDLBERGER、Karl-Heinz DEIMER

  DOI：10.1515/bchm2.1976.357.1.447

  日期：1976.1
• GOODNOW, R. (JR);KONNO, K.;NIWA, M.;KALLIMOPOULOS, T.;BUKOWNIK, R.;LENARE+, TETRAHEDRON, 46,(1990) N, C. 3267-3286
  作者：GOODNOW, R. (JR)、KONNO, K.、NIWA, M.、KALLIMOPOULOS, T.、BUKOWNIK, R.、LENARE+

  DOI：——

  日期：——
• CLAESSON, ALF;JANSSON, ANITA M.;PRING, BRIAN G.;HAMMOND, STEPHEN M.;EKSTR+, J. MED. CHEM., 30,(1987) N 12, 2309-2313
  作者：CLAESSON, ALF、JANSSON, ANITA M.、PRING, BRIAN G.、HAMMOND, STEPHEN M.、EKSTR+

  DOI：——

  日期：——