tryptophanyl-valine methyl ester | 53848-98-9

• 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: tryptophanyl-valine methyl ester
• 英文别名: H-Trp-Val-OMe；methyl (2S)-2-[[(2S)-2-amino-3-(1H-indol-3-yl)propanoyl]amino]-3-methylbutanoate
• CAS: 53848-98-9
• 化学式: C₁₇H₂₃N₃O₃
• 分子量: 317.388
• InChiKey: JPMNNMZMIYCVGZ-ZFWWWQNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  97.2
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tryptophanyl-valine methyl ester 在 palladium diacetate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 对苯醌 作用下， 以 1,4-二氧六环 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Late-stage construction of stapled peptides through Fujiwara–Moritani reaction between tryptophan and olefins

  摘要：

  这里，首次展示了一种钯催化的Fujiwara-Moritani反应的例子，用于无需定向基团的色氨酸（Trp）残基的烯化。

  DOI：

  10.1039/d1cc04202e
• 作为产物：
  描述：

  N-叔丁氧羰基-L-色氨酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 tryptophanyl-valine methyl ester
  参考文献：
  名称：

  含色氨酸肽的铁催化仿生二聚化

  摘要：

  八羧基酞菁铁络合物催化的色氨酸衍生物的仿生氧化二聚反应是在水性介质中以氧作为本体氧化剂建立的。该协议允许对具有显着功能组耐受性的各种含色氨酸肽进行二聚化，以构建天然和非天然的吡咯并吲哚二聚体和二聚化肽，并具有连接两个转弯结构的独特支架。

  DOI：

  10.1002/anie.202302404

文献信息

• Gold-catalyzed direct alkynylation of tryptophan in peptides using TIPS-EBX
  作者：Gergely L Tolnai、Jonathan P Brand、Jerome Waser

  DOI：10.3762/bjoc.12.74

  日期：——

  biomolecules. In particular, the installation of an alkyne as a useful handle for bioconjugation is highly attractive, but the use of a carbon linker is usually required. Herein, we report the gold-catalyzed direct alkynylation of tryptophan in peptides using the hypervalent iodine reagent TIPS-EBX (1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one). The reaction proceeded in 50-78% yield under

  仅包含天然氨基酸的肽的选择性功能化对于修饰生物分子很重要。特别地，将炔烃作为用于生物缀合的有用手柄的安装极具吸引力，但是通常需要使用碳连接基。在此，我们报告了使用高价碘试剂TIPS-EBX（1-[（三异丙基甲硅烷基）乙炔基] -1，2-苯并恶多酚-3（1H）-一）在肽中金催化的色氨酸直接烷基化。反应在温和的条件下以50-78％的收率进行，可用于含有其他亲核和芳香族氨基酸（如丝氨酸，苯丙氨酸或酪氨酸）的肽。
• Peptides
  申请人：Farmitalia Carlo Erba

  公开号：US04491541A1

  公开（公告）日：1985-01-01

  A peptide of formula (I): X-A-B-C-Trp-D-Y wherein X represents hydrogen, or a terminal nitrogn protecting group selecting from the group consisting of the acyl, aromatic oxycarbonyl, alkyl, aralkyl and aliphatic oxycarbonyl; A represent a valence bond or a L-.alpha.-amino acid residue; B represent a L-.alpha.-imino acid residue or a L-.alpha.-amino acid; C represent a L-.alpha.-imino acid residue or a neutral L-.alpha.-amino acid residue; D represents a valence bond or a L-.alpha.-amino acid residue; and Y represents hydroxy, an amino group or a group of the formula OR, NHR, NR.sub.2 or NH--NH--R', wherein R represents a straight chain, branched chain or cyclic (including fused or bridged ring) alkyl group having up to 11 carbon atoms, optionally being substituted; a phenyl group or an aralkyl group having from 7 to 9 carbon atoms; and R' represents hydrogen, any of the groups which R may represent; a straight chain, branched chain or cyclic aliphatic acyl group having from 1 to 11 carbon atoms, optionally substituted by hydroxy, an amino group or a halogen atom; an aromatic acyl group, optionally substituted by hydroxy, amino, or a halogen atom; a straight chain, branched chain or cyclic aliphatic oxycarbonyl group having from 3 to 11 carbon atoms, or an aromatic oxycarbonyl group.

  化合物的肽式(I)：X-A-B-C-Trp-D-Y，其中X代表氢或末端氮保护基，选择自酰基、芳香氧羰基、烷基、芳基烷基和脂肪氧羰基的群；A代表一个价键或L-α-氨基酸残基；B代表L-α-亚氨基酸残基或L-α-氨基酸；C代表L-α-亚氨基酸残基或中性L-α-氨基酸残基；D代表一个价键或L-α-氨基酸残基；Y代表羟基、氨基或公式OR、NHR、NR2或NH--NH--R'的基团，其中R代表直链、支链或环状（包括融合或桥接环）碳原子数高达11个的烷基，可以选择性地被取代；苯基或具有7到9个碳原子的芳基烷基；R'代表氢、R可能代表的任何基团；具有1到11个碳原子的直链、支链或环状脂肪酰基，可以选择性地被羟基、氨基或卤素原子取代；芳香酰基，可以选择性地被羟基、氨基或卤素原子取代；具有3到11个碳原子的直链、支链或环状脂肪氧羰基基团，或芳香氧羰基基团。
• Belagali; Himaja, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 4, p. 505 - 507
  作者：Belagali、Himaja

  DOI：——

  日期：——
• Selective Inhibitors of the Serine Protease Plasmin:  Probing the S3 and S3‘ Subsites Using a Combinatorial Library
  作者：Fengtian Xue、Christopher T. Seto

  DOI：10.1021/jm050488k

  日期：2005.11.1

  A combinatorial library of 400 serine protease inhibitors with the general structure Cbz-X-aa-Trp-cyclohexanone-Trp-Y-aa-OH has been constructed. The library was synthesized on the solid phase using mix-and-split synthesis, where 20 different amino acids were incorporated at both the X-aa and Y-aa positions. These two positions correspond to the S3 and S3' subsites of the active site. Iterative deconvolution was used to identify hits from the library. The library was screened against four serine proteases: plasmin, kallikrein, thrombin, and trypsin. Seven inhibitors from the library that showed promising activities were resynthesized using solutionphase methods. Four of these compounds were good inhibitors of plasmin with IC50 values in the range of 2.7 - 3.6 mu M. The most potent of these inhibitors showed > 150-fold selectivity for plasmin when compared to the other three serine proteases.
• Thioacetic Acid/NaSH-Mediated Synthesis of <i>N</i>-Protected Amino Thioacids and Their Utility in Peptide Synthesis
  作者：Sachitanand M. Mali、Hosahudya N. Gopi

  DOI：10.1021/jo402872p

  日期：2014.3.21

  Thioacids are recently gaining momentum due to their versatile reactivity. The reactivity of thioacids has been widely explored in the selective amide/peptide bond formation. Thioacids are generally synthesized from the reaction between activated carboxylic acids such as acid chlorides, active esters, etc., and Na2S, H2S, or NaSH. We sought to investigate whether the versatile reactivity of the thioacids can be tuned for the conversion of carboxylic acids into corresponding thioacids in the presence of NaSH. Herein, we report that thioacetic acid- and NaSH-mediated synthesis of N-protected amino thioacids from the corresponding N-protected amino acids, oxidative dimerization of thioacids, crystal conformations of thioacid oxidative dimers, and the utility of thioacids and oxidative dimers in peptide synthesis. Our results suggest that peptides can be synthesized without using standard coupling agents.