N-acetyl-2-methyltryptophan | 60587-01-1

• 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: N-acetyl-2-methyltryptophan
• 英文别名: 2-acetamido-3-(2-methyl-1H-indol-3-yl)propanoic acid
• CAS: 60587-01-1
• 化学式: C₁₄H₁₆N₂O₃
• 分子量: 260.293
• InChiKey: VXPVVVOPIDJJSM-UHFFFAOYSA-N

物化性质

• 沸点：
  585.1±50.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-acetyl-2-methyltryptophan 在 barium dihydroxide 作用下， 反应 30.0h， 生成 2-甲基-DL-色氨酸
  参考文献：
  名称：

  Fluorescence Studies with Tryptophan Analogs: Excited State Interactions Involving the Side Chain Amino Group

  摘要：

  The fluorescence of a large set of tryptophan analogues, including several that are conformationally constrained, was studied. The constrained analogues include tetrahydrocarboline-3-carboxylic acid and 3-amino-3-carboxytetrahydrocarbazole. Steady state and time-resolved fluorescence measurements were made as a function of pH. The fluorescence quantum yields of the constrained analogues are higher than those for the unconstrained counterparts. The emission intensity of the constrained analogues, as well as 4-methyltryptophan, decreases with deprotonation of the side chain alpha-ammonium group; this is in contrast to the increase in fluorescence of tryptophan with deprotonation of this group. These results are consistent with the existence of excited state proton transfer to carbon 4 of the indole ring as a quenching mechanism, which is sterically prohibited in the constrained analogues and 4-methyltryptophan. From quantum yield and lifetime data (most decays are nonexponential), the effective rate constant for nonradiative depopulation of the excited state was calculated. For tryptophan analogues having two side chain functional groups, there is a synergistic effect; the presence of two side chain groups causes more quenching than expected from the sum of the individual contributions. For analogues having ana-ammonium group, this synergism appears to be correlated with an induced change in the pK(alpha) of this group. Deprotonation of this cl-ammonium group also causes a red shift in the emission of these compounds; this appears to be due to electrostatic repulsion between the alpha-NH3+ group and the excited indole dipole.

  DOI：

  10.1021/j100015a064
• 作为产物：
  描述：

  acetylamino-(2-methyl-indol-3-ylmethyl)-malonic acid 在 氮气 作用下， 生成 N-acetyl-2-methyltryptophan
  参考文献：
  名称：

  141.核-C-甲基化色氨酸的合成。关于色氨酸醛反应的注释

  摘要：

  DOI：

  10.1039/jr9480000705

文献信息

• Mechanistic Studies on Tryptophan Lyase (NosL): Identification of Cyanide as a Reaction Product
  作者：Dhananjay M. Bhandari、Dmytro Fedoseyenko、Tadhg P. Begley

  DOI：10.1021/jacs.7b09000

  日期：2018.1.17

  Tryptophan lyase (NosL) catalyzes the formation of 3-methylindole-2-carboxylic acid and 3-methylindole from l-tryptophan. In this paper, we provide evidence supporting a formate radical intermediate and demonstrate that cyanide is a byproduct of the NosL-catalyzed reaction with l-tryptophan. These experiments require a major revision of the NosL mechanism and uncover an unanticipated connection between

  色氨酸裂解酶 (NosL) 催化 3-甲基吲哚-2-羧酸和 3-甲基吲哚从 l-色氨酸形成。在本文中，我们提供了支持甲酸自由基中间体的证据，并证明氰化物是 NosL 催化与 l-色氨酸反应的副产物。这些实验需要对 NosL 机制进行重大修改，并揭示 NosL 和 HydG 之间的意外联系，HydG 是一种自由基 SAM 酶，在 [Fe-Fe] 氢化酶的金属簇生物合成过程中，由酪氨酸形成氰化物和一氧化碳。
• Studies on indolic mould metabolites. Total synthesis of l-prolyl-2-methyltryptophan anhydride and deoxybrevianamide e
  作者：R. Ritchie、J.E. Saxton

  DOI：10.1016/0040-4020(81)85025-9

  日期：1981.1

  Syntheses of l - prolyl - 2 - methyl - l - tryptophan anhydride, l -prolyl - 2 - methyl - d - tryptophan anhydride, deoxybrevianamide E, and l - prolyl - 2 - (1,1 - dimethylallyl) - d- tryptophan anhydride are described. A route for the conversion of deoxybrevianamide E into brevianamide E has also been examined.

  1-prolyl-2-甲基-1-色氨酸酐，1-prolyl-2-甲基-d-色氨酸酐，脱氧布雷维酰胺E和1-prolyl-2-（1,1-二甲基烯丙基）-d-色氨酸酐的合成被描述。还研究了将脱氧布雷维酰胺E转化为布雷维酰胺E的途径。
• D-2-alkyl-tryptophan and peptides containing same
  申请人：Deghenghi; Romano

  公开号：US05635379A1

  公开（公告）日：1997-06-03

  Peptides containing in its amino acid chain a D-2-alkylTryptophan residue wherein the alkyl group has between one and three carbon atoms and having pharmacological activity similar to that of analogous peptides containing natural unsubstituted D-Tryptophan residues in place of the D-2-alkylTryptophan. These new peptides are more resistant to oxidative degradation which usually takes place, for example, in the presence of reactive radicals or during high energy sterilization than unsubstituted Tryptophan containing peptides. Specific peptides include His-D-2-alkyl-Trp-Ala-Trp-D-Phe-Lys-NH.sub.2, Ala-His-D-2-alkyl-Trp-Ala-Trp-D-Phe-Lys-NH.sub.2, Pyro-Glu-His-Trp-Ser-Tyr-D-2-alkyl-Trp-Leu-Arg-Pro-Gly-NH.sub.2, Pyro-Glu-His-Ser-Tyr-D-2-alkyl-Trp-Leu-Arg-Pro-NHCH.sub.2 CH.sub.3, D-Pro-Gln-Gln-D-Trp-Phe-D-Trp-2-alkyl-Trp-Met-NH.sub.2, Arg-D-Trp-N-methyl-Phe-D-2-alkyl-Trp-Leu-Met-NH.sub.2, D-Phe-Cys-Phe-D-2-alkyl-Trp-Lys-Thr-Cys-NHCH(CH.sub.2 OH)CHOHCH.sub.3 and D-Phe-Cys-Tyr-D-2-alkyl-Trp-Lys-Val-Cys-Trp-NH.sub.2.

  这些肽包含一个D-2-烷基色氨酸残基的氨基酸链，其中烷基基团含有一到三个碳原子，并具有与含有未取代的D-色氨酸残基的类似肽相似的药理活性。这些新肽比含有未取代色氨酸的肽更耐氧化降解，例如，在反应性自由基存在或高能灭菌过程中通常会发生这种降解。特定的肽包括His-D-2-烷基-Trp-Ala-Trp-D-Phe-Lys-NH.sub.2，Ala-His-D-2-烷基-Trp-Ala-Trp-D-Phe-Lys-NH.sub.2，Pyro-Glu-His-Trp-Ser-Tyr-D-2-烷基-Trp-Leu-Arg-Pro-Gly-NH.sub.2，Pyro-Glu-His-Ser-Tyr-D-2-烷基-Trp-Leu-Arg-Pro-NHCH.sub.2 CH.sub.3，D-Pro-Gln-Gln-D-Trp-Phe-D-Trp-2-烷基-Trp-Met-NH.sub.2，Arg-D-Trp-N-甲基-Phe-D-2-烷基-Trp-Leu-Met-NH.sub.2，D-Phe-Cys-Phe-D-2-烷基-Trp-Lys-Thr-Cys-NHCH(CH.sub.2 OH)CHOHCH.sub.3和D-Phe-Cys-Tyr-D-2-烷基-Trp-Lys-Val-Cys-Trp-NH.sub.2。
• D-2-alkyl tryptophan compounds
  申请人：Deghenghi; Romano

  公开号：US05646301A1

  公开（公告）日：1997-07-08

  D-2-Alkyl Tryptophan compounds for incorporation into various peptides during manufacture thereof or for substitution for D-Tryptophan residues in such peptides to provide a D-2-alkyl Tryptophan residue therein which enhances the stability and biological activity of the peptide.

  D-2-烷基色氨酸化合物可用于在制造过程中并入各种肽中，或替换这些肽中的D-色氨酸残基，以提供其中的D-2-烷基色氨酸残基，从而增强肽的稳定性和生物活性。
• Peptides containing D-2-Alkyl-Tryptophan
  申请人：——

  公开号：US05872100A1

  公开（公告）日：1999-02-16

  Peptides containing in its amino acid chain a D-2-alkylTryptophan residue wherein the alkyl group has between one and three carbon atoms and having pharmacological activity equal to or greater than that of analogous peptides containing natural unsubstituted D-Tryptophan residues in place of the D-2-alkylTryptophan. These peptides are more resistant to oxidative degradation which usually takes place, for example, in the presence of reactive radicals or during high energy sterilization than unsubstituted Tryptophan containing peptides.

  肽链中含有D-2-烷基色氨酸残基的肽，其中烷基基团具有一到三个碳原子，并具有与含有天然未取代的D-色氨酸残基的类似肽相等或更大的药理活性。这些肽比含有未取代色氨酸的肽更耐氧化降解，例如，在反应性自由基存在或高能灭菌期间通常发生。