dansyl-GCVLS | 143744-88-1

• 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: dansyl-GCVLS
• 英文别名: N-dansyl-GCVLS；Dansyl-Gly-Cys-Val-Leu-Ser-OH；(2S)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[2-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]acetyl]amino]-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxypropanoic acid
• CAS: 143744-88-1
• 化学式: C₃₁H₄₆N₆O₉S₂
• 分子量: 710.873
• InChiKey: PYFRGABQIDFXHO-FAWUNYRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  48
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  233
• 氢给体数：
  8
• 氢受体数：
  12

安全信息

• 储存条件：
  室温

制备方法与用途

Dansyl-Gly-Cys-Val-Leu-Ser是一种丹酰基标记肽。

反应信息

• 作为反应物：
  描述：

  farnesyl pyrophosphate 、 dansyl-GCVLS 在 rat protein farnesyltransferase 作用下， 生成 dansyl-G(S-farnesyl)CVLS
  参考文献：
  名称：

  Synthesis of acyloxymethyl ester prodrugs of the transferable protein farnesyl transferase substrate farnesyl methylenediphosphonate

  摘要：

  Three isoprenoid diphosphate analogues of farnesyl diphosphate (FPP) where the diphosphate has been replaced by methylene diphosphonate and the negative charges masked by frangible pivaloyloxymethyl (POM) esters were prepared. Farnesyl methylenediphosphonate is a sub-micromolar substrate for protein farnesyl transferase. The tripivaloyloxymethyl esters of isoprenoid methylenediphosphonate have significantly increased lipophilicity and may act as important farnesyl diphosphate prodrugs. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.017
• 作为产物：
  描述：

  Fmoc-L-缬氨酸 、 Fmoc-L-亮氨酸 、 丹磺酰甘氨酸 、 Fmoc-S-三苯甲基-L-半胱氨酸 、 alkaline earth salt of/the/ methylsulfuric acid 生成 dansyl-GCVLS
  参考文献：
  名称：

  Evaluation of protein farnesyltransferase substrate specificity using synthetic peptide libraries

  摘要：

  Farnesylation, catalyzed by protein farnesyltransferase (FTase), is an important post-translational modification guiding cellular localization. Recently predictive models for identifying FTase substrates have been reported. Here we evaluate these models through screening of dansylated-GCaaS peptides, which also provides new insights into the protein substrate selectivity of FTase. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.08.024

文献信息

• Photoaffinity Analogues of Farnesyl Pyrophosphate Transferable by Protein Farnesyl Transferase
  作者：Kareem A. H. Chehade、Katarzyna Kiegiel、Richard J. Isaacs、Jennifer S. Pickett、Katherine E. Bowers、Carol A. Fierke、Douglas A. Andres、H. Peter Spielmann

  DOI：10.1021/ja0124717

  日期：2002.7.1

  followed by ester hydrolysis, chlorination, and pyrophosphorylation. Additional substitution of three methylenes for the beta-isoprene of FPP gave photoprobe 6 in nine steps. Preparation of the analogues required TiCl(4)-mediated imine formation prior to NaBH(OAc)(3) reduction for anilines with a pK(a) < 1. The azide moiety was not affected by Ph(3)PCl(2) conversion of allylic alcohols 13-16 into corresponding

  Farnesylation 是一种翻译后脂质修饰，其中 15 个碳的法呢基异戊二烯通过硫醚键连接到蛋白质的特定半胱氨酸残基，在由蛋白质法呢基转移酶 (FTase) 催化的反应中进行。我们合成了焦磷酸法呢酯 (FPP) 的类似物 (3-6)，以探测 FPP 骨架可能发生的修饰范围，从而允许 FTase 进行有效转移。FPP 的光亲和类似物 (5, 6) 是通过用全氟苯基叠氮化物官能团取代 FPP 的 omega 末端异戊二烯来制备的。取代的苯胺取代了类似物 3 和 4 中的 ω-末端异戊二烯。化合物 3-5 是通过用 8-氧代-香叶基乙酸酯还原胺化适当的苯胺，然后进行酯水解、氯化和焦磷酸化来制备的。三个亚甲基对 FPP 的 β-异戊二烯的额外取代在九个步骤中产生了光探针 6。对于 pK(a) < 1 的苯胺，在 NaBH(OAc)(3) 还原之前，制备类似物需要 TiCl(4) 介导的亚胺形成。叠氮化物部分不受
• Synthesis, Enzymatic Peptide Incorporation, and Applications of Diazirine-Containing Isoprenoid Diphosphate Analogues
  作者：Katarzyna Justyna、Riki Das、Ellen L. Lorimer、Jiayue Hu、Jodi S. Pedersen、Andrea M. Sprague-Getsy、Garrett L. Schey、Michelle A. Sieburg、Olivia J. Koehn、Yen-Chih Wang、Yong-Xiang Chen、James L. Hougland、Carol L. Williams、Mark D. Distefano

  DOI：10.1021/acs.orglett.3c02736

  日期：2023.9.15

  near their C-termini. Here we describe the preparation of isoprenoid diphosphate analogues incorporating diazirine groups that can be used to probe interactions between prenylated proteins and other proteins that interact with them. Studies using synthetic peptides and whole proteins demonstrate that these diazirine analogues are efficient substrates for prenyltransferases. Photo-cross-linking experiments

  异戊二烯化蛋白质含有与其 C 末端附近的半胱氨酸残基相连的 C 15或 C 20 类异戊二烯。在这里，我们描述了掺入二氮丙啶基团的类异戊二烯二磷酸类似物的制备，该类似物可用于探测异戊二烯化蛋白质和与其相互作用的其他蛋白质之间的相互作用。使用合成肽和完整蛋白质的研究表明，这些二氮丙啶类似物是异戊二烯基转移酶的有效底物。使用掺有二氮丙啶功能化类异戊二烯的肽进行光交联实验，选择性地与几种不同的蛋白质交联。这些新的类异戊二烯类似物应该广泛用于蛋白质异戊二烯化的研究。
• Synthesis and In Vitro Evaluation of the Farnesyltransferase Inhibitor Pepticinnamin E
  作者：Klaus Hinterding、Patrizia Hagenbuch、Janos Rétey、Herbert Waldmann

  DOI：10.1002/(sici)1521-3765(19990104)5:1<227::aid-chem227>3.3.co;2-o

  日期：1999.1.4
• US5525479A
  申请人：——

  公开号：US5525479A

  公开（公告）日：1996-06-11
• Synthesis of acyloxymethyl ester prodrugs of the transferable protein farnesyl transferase substrate farnesyl methylenediphosphonate
  作者：Jerry M. Troutman、Kareem A.H. Chehade、Katarzyna Kiegiel、Douglas A. Andres、H. Peter Spielmann

  DOI：10.1016/j.bmcl.2004.07.017

  日期：2004.10

  Three isoprenoid diphosphate analogues of farnesyl diphosphate (FPP) where the diphosphate has been replaced by methylene diphosphonate and the negative charges masked by frangible pivaloyloxymethyl (POM) esters were prepared. Farnesyl methylenediphosphonate is a sub-micromolar substrate for protein farnesyl transferase. The tripivaloyloxymethyl esters of isoprenoid methylenediphosphonate have significantly increased lipophilicity and may act as important farnesyl diphosphate prodrugs. (C) 2004 Elsevier Ltd. All rights reserved.