L-tryptophan | 6536-35-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: L-tryptophan
• 英文别名: S-tryptophan；H-L-Trp-OH；tryptophan；L-Trp；L-tryptophane；(2S)-2-amino-3-(3H-indol-3-yl)propanoic acid
• CAS: 6536-35-2
• 化学式: C₁₁H₁₂N₂O₂
• 分子量: 204.228
• InChiKey: RDTOURARQPNLFK-NETXQHHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  75.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-tryptophan 生成 α,β-dehydrotryptophan
  参考文献：
  名称：

  Genet, R; Denoyelle, C; Menez, A, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 12, p. 848 - 850

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯-6-硝基甲苯 在 镍 磷化氢 、 sodium hydroxide 、 氢碘酸 、 氢气 、 乙酸酐 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 25.0~120.0 ℃ 、10.34 MPa 条件下， 反应 165.25h， 生成 L-tryptophan
  参考文献：
  名称：

  S-4-chlorotryptophan: Its synthesis via resolution, determination of the absolute stereochemistry and identification in the crude seed protein of the pea, pisum sativum

  摘要：

  DOI：

  10.1016/s0040-4039(00)86054-2

文献信息

• Modified amino acids
  申请人：Technische Universität Wien

  公开号：EP1826199A1

  公开（公告）日：2007-08-29

  The present invention provides a compound of the general formula 1, wherein X is the connection between the CO-hydrazine and the NR1-oxalic acid or ester group, and uses and synthesis methods. These compounds represent amino acid derivatives, wherein the amine group is turned into an acidic group by the oxalic acid group and the carboxylic acid is turned into an amine functionality by the hydrazine group; as well as peptidomimetics comprising the compound and methods for their synthesis.

  本发明提供了一种一般式1的化合物， 其中X是CO-肼和NR1-草酸或酯基之间的连接，并提供了使用和合成方法。这些化合物代表氨基酸衍生物，其中氨基团通过草酸基转化为酸性基团，羧酸通过肼基转化为氨基功能团；以及包括该化合物的肽类似物和其合成方法。
• Investigation of Vanadocene(IV) α-Amino Acid Complexes:  Synthesis, Structure, and Behavior in Physiological Solutions, Human Plasma, and Blood
  作者：Jaromír Vinklárek、Hana Paláčková、Jan Honzíček、Jana Holubová、Michal Holčapek、Ivana Císařová

  DOI：10.1021/ic050687u

  日期：2006.3.1

  characterized by X-ray structure analyses. It was evidenced that all prepared complexes are stable in both aqueous solutions with physiological pH and in therapeutic NaCl solutions. EPR spectra of vanadocene amino acid complexes in Krebs-Ringer solution in human blood plasma and in whole blood showed that these complexes react with the hydrogen carbonate anion present forming complex Cp2V(O2CO).

  这项工作的重点是研究在生理pH值下水溶液中氨基酸的抗肿瘤活性金属茂钒二氯化碳（Cp2VCl2）与氨基酸之间的相互作用。制备了十六种钒氧烯氨基酸复合物[Cp2V（aa）] [X]（aa = gly，ala，val，leu，ile，phe，his和his trp； X = Cl，PF6），并根据光谱测量进行了表征（EPR，MS，IR，拉曼）。氨基酸通过羧基的氧原子和氨基的氮与钒二烯片段配位，形成五元螯合环。配合物[Cp2V（val）] [PF6]和[Cp2V（ile）] [PF6]已通过X射线结构分析进行了表征。证明所有制备的复合物在具有生理pH的水溶液和治疗性NaCl溶液中都是稳定的。
• The Modification of Tryptophyl Residues during the Acidolytic Cleavage of Boc-groups. I. Studies with Boc-Tryptophan
  作者：Yoshihiro Masui、Naoyoshi Chino、Shumpei Sakakibara

  DOI：10.1246/bcsj.53.464

  日期：1980.2

  The formation of a component, X, was observed when a reaction mixture of t-butyloxycarbonyl-tryptophan (Boc-Trp), trifluoroacetic acid (TFA), and 1,2-ethanedithiol was analyzed by cellulose TLC. The side product was isolated and further separated into two components by column chromatography on silica gel. The subsequent analysis of the NMR spectra of these components confirmed that they were Nin-But-Trp and Cin-But-Trp. The reaction of Boc-Trp with TFA and with anhydrous hydrogen fluoride (HF) was examined as model systems in order to determine conditions which would minimize the formation of the X component during the synthesis of peptides containing Trp. The addition of 10 molar equivalents of 1,2-ethanedithiol completely suppressed the formation of the X component in HF, but additives were less efficient in TFA. A combination of dimethyl sulfide and 1,2-ethanedithiol was the most effective method for suppressing the formation of the X component in TFA. The behavior of Nin- and Cin-But-Trp in acidic media was also investigated, and a possible pathway for the t-butylation of the tryptophyl residue will be proposed.

  通过纤维素薄层色谱法分析叔丁氧羰基-色氨酸（Boc-Trp）、三氟乙酸（TFA）和1,2-乙二硫醇的反应混合物时，观察到了成分X的形成。通过硅胶柱色谱法分离并进一步分离出两种成分。随后对这些成分的核磁共振光谱进行分析，证实它们分别是Nin-But-Trp和Cin-But-Trp。为了确定在合成含色氨酸的肽时，如何将X成分的形成降到最低，以Boc-Trp与TFA和氟化氢（HF）的反应作为模型系统进行了研究。在HF中，添加10摩尔当量的1,2-乙二硫醇完全抑制了X成分的形成，但在TFA中，添加剂的效果较差。二甲基硫醚和1,2-乙二硫醇的组合是抑制TFA中X成分形成的最有效方法。还研究了Nin-But-Trp和Cin-But-Trp在酸性介质中的行为，并提出了色氨酸残基叔丁基化的可能途径。
• Genet, R; Denoyelle, C; Menez, A, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 12, p. 848 - 850
  作者：Genet, R、Denoyelle, C、Menez, A

  DOI：——

  日期：——
• S-4-chlorotryptophan: Its synthesis via resolution, determination of the absolute stereochemistry and identification in the crude seed protein of the pea, pisum sativum
  作者：S.V. Thiruvikraman、Youji Sakagami、Masato Katayama、Shingo Marumo

  DOI：10.1016/s0040-4039(00)86054-2

  日期：——