DL-4-Nitro-N-acetyl-tryptophan | 91768-84-2

• 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: DL-4-Nitro-N-acetyl-tryptophan
• 英文别名: 4-Nitro-N-acetyl-tryptophan；N-acetyl-4-nitrotryptophan；N-Acetyl-4-nitro-L-tryptophan；2-acetamido-3-(4-nitro-1H-indol-3-yl)propanoic acid
• CAS: 91768-84-2
• 化学式: C₁₃H₁₃N₃O₅
• 分子量: 291.263
• InChiKey: PPBXRRAOLBQTEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  128
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  DL-4-Nitro-N-acetyl-tryptophan 在 palladium on activated charcoal 盐酸 、 氢氧化钾 、 锂硼氢 、 氯化亚砜 、 氢气 、 碳酸氢钠 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 100.5h， 生成 [[3-(2-Amino-3-hydroxy-propyl)-1H-indol-4-yl]-(4-nitro-benzyloxycarbonyl)-amino]-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester
  参考文献：
  名称：

  Molecular requirements for epigenetic modulators. Synthesis of active fragments of teleocidins and lyngbyatoxin.

  摘要：

  本文介绍了 3、4、5、6、7、8-六氢-6-氧代[1，4] 重氮诺[7，6，5-cd]吲哚（3 和 18）的合成，它们具有 teleocidins（1）和 lyngbyatoxin（2）的活性片段。

  DOI：

  10.1248/cpb.30.3457
• 作为产物：
  描述：

  4-硝基芦竹碱 在 sodium ethanolate 、 碘乙烷 作用下， 以 sodium hydroxide 、 乙醇 、 水 为溶剂， 反应 9.5h， 生成 DL-4-Nitro-N-acetyl-tryptophan
  参考文献：
  名称：

  Molecular requirements for epigenetic modulators. Synthesis of active fragments of teleocidins and lyngbyatoxin.

  摘要：

  本文介绍了 3、4、5、6、7、8-六氢-6-氧代[1，4] 重氮诺[7，6，5-cd]吲哚（3 和 18）的合成，它们具有 teleocidins（1）和 lyngbyatoxin（2）的活性片段。

  DOI：

  10.1248/cpb.30.3457

文献信息

• Synthesis and NMR characteristics of <i>N</i> -acetyl-4-nitro, <i>N</i> -acetyl-5-nitro, <i>N</i> -acetyl-6-nitro and <i>N</i> -acetyl-7-nitrotryptophan methyl esters
  作者：Russell R. King、Larry A. Calhoun

  DOI：10.1002/mrc.2377

  日期：2009.3

  N‐acetyl‐4‐nitrotryptophan methyl ester (2), N‐acetyl‐5‐nitrotryptophan methyl ester (3), N‐acetyl‐6‐nitrotryptophan methyl ester (4) and N‐acetyl‐7‐nitrotryptophan methyl ester (5) were synthesized through a modified malonic ester reaction of the appropriate nitrogramine analogs followed by methylation with BF3‐methanol. Assignments of the 1H and 13C NMR chemical shifts were made using a combination

  N-乙酰基-4-硝基色氨酸甲酯（2）、N-乙酰基-5-硝基色氨酸甲酯（3）、N-乙酰基-6-硝基色氨酸甲酯（4）和N-乙酰基-7-硝基色氨酸甲酯（5 ) 是通过适当的硝基甘氨酸类似物的改性丙二酸酯反应合成的，然后用 BF3-甲醇进行甲基化。1H 和 13C NMR 化学位移的分配是使用 1H-1H COSY、1H-13C HETCOR 和 1H-13C 选择性 INEPT 实验的组合进行的。版权所有 © 2008 Crown 归加拿大所有。由 John Wiley & Sons, Ltd 出版
• [EN] METHODS FOR THAXTOMIN PRODUCTION AND ENGINEERED NON-NATIVE STREPTOMYCES WITH INCREASED THAXTOMIN PRODUCTION<br/>[FR] PROCÉDÉS DE PRODUCTION DE THAXTOMINE ET STREPTOMYCES MODIFIÉ NON NATIF PRÉSENTANT UNE PRODUCTION ACCRUE DE THAXTOMINE
  申请人：UNIV FLORIDA

  公开号：WO2018217855A1

  公开（公告）日：2018-11-29

  The present disclosure includes genetically engineered, non-pathogenic Streptomyces bacterium with exogenous, non-native Thaxtomin A (ThxA) biosynthetic gene clusters conferring the genetically engineered, non-pathogenic Streptomyces bacterium with the ability to produce thaxtomin A. Also included are methods of providing thaxtominproducing capability in non-native Streptomyces bacterial strains, methods of producing thaxtomin compounds with the genetically engineered Streptomyces bacteria of the present disclosure, and methods of producing thaxtomin compounds and nitro-tryptophan analogs, and fluorinated thaxtomin compounds, analogs, and intermediates with the genetically engineered Streptomyces bacteria of the present disclosure.

  本公开涉及具有外源非自然Thaxtomin A（ThxA）生物合成基因簇的基因工程非致病链霉菌，使得这些基因工程非致病链霉菌具有生产thaxtomin A的能力。还包括在非自然链霉菌菌株中提供生产thaxtomin的能力的方法，使用本公开的基因工程链霉菌生产thaxtomin化合物的方法，以及使用本公开的基因工程链霉菌生产thaxtomin化合物、硝基色氨酸类似物和氟代thaxtomin化合物、类似物和中间体的方法。
• US11530415B2
  申请人：University of Florida Research Foundation, Inc.

  公开号：US11530415B2

  公开（公告）日：2022-12-20

  The present disclosure includes refactored thaxtomin biosynthetic gene clusters including thaxtomin modules including one or more thaxtomin genes such that the expression of the refactored thaxtomin biosynthetic gene cluster produces at least one thaxtomin compound in the absence of thaxtomin-inducing conditions. Also included are genetically engineered Streptomyces bacterium from a non-pathogenic Streptomyces strain comprising an exogenous, refactored thaxtomin biosynthetic gene cluster of the present disclosure, such that the expression of the refactored thaxtomin biosynthetic gene cluster provides the genetically engineered Streptomyces bacterium with the ability to produce at least one thaxtomin compound in the absence of thaxtomin-inducing conditions. The present disclosure also includes methods of producing thaxtomin compounds, analogs, or intermediate with the refactored thaxtomin biosynthetic gene clusters and genetically engineered bacteria of the present disclosure.

  本公开内容包括重构的刺五加生物合成基因簇，其中的刺五加模块包括一个或多个刺五加基因，从而使重构的刺五加生物合成基因簇的表达能在没有刺五加诱导条件下产生至少一种刺五加化合物。还包括基因工程改造的 链霉菌 的基因工程链霉菌。 链霉菌 菌株的基因工程链霉菌，该菌株包含本公开的外源的、经过重构的硫司多明生物合成基因簇，这样，经过重构的硫司多明生物合成基因簇的表达为基因工程链霉菌提供了 链霉菌 细菌，使其有能力在没有他克莫明诱导条件下生产至少一种他克莫明化合物。本公开还包括利用本公开的重构的噻吨胺生物合成基因簇和基因工程细菌生产噻吨胺化合物、类似物或中间体的方法。
• METHODS FOR THAXTOMIN PRODUCTION AND ENGINEERED NON-NATIVE STREPTOMYCES WITH INCREASED THAXTOMIN PRODUCTION
  申请人：University of Florida Research Foundation, Inc.

  公开号：US20200140905A1

  公开（公告）日：2020-05-07

  The present disclosure includes genetically engineered, non-pathogenic Streptomyces bacterium with exogenous, non-native Thaxtomin A (ThxA) biosynthetic gene clusters conferring the genetically engineered, non-pathogenic Streptomyces bacterium with the ability to produce thaxtomin A. Also included are methods of providing thaxtomin producing capability in non-native Streptomyces bacterial strains, methods of producing thaxtomin compounds with the genetically engineered Streptomyces bacteria of the present disclosure, and methods of producing thaxtomin compounds and nitro-tryptophan analogs, and fluorinated thaxtomin compounds, analogs, and intermediates with the genetically engineered Streptomyces bacteria of the present disclosure.
• METHODS FOR THAXTOMIN PRODUCTION IN ENGINEERED NON-NATIVE STREPTOMYCES IN THE ABSENCE OF CELLOBIOSE
  申请人：University of Florida Research Foundation, Inc.

  公开号：US20200362298A1

  公开（公告）日：2020-11-19

  The present disclosure includes refactored thaxtomin biosynthetic gene clusters including thaxtomin modules including one or more thaxtomin genes such that the expression of the refactored thaxtomin biosynthetic gene cluster produces at least one thaxtomin compound in the absence of thaxtomin-inducing conditions. Also included are genetically engineered Streptomyces bacterium from a non-pathogenic Streptomyces strain comprising an exogenous, refactored thaxtomin biosynthetic gene cluster of the present disclosure, such that the expression of the refactored thaxtomin biosynthetic gene cluster provides the genetically engineered Streptomyces bacterium with the ability to produce at least one thaxtomin compound in the absence of thaxtomin-inducing conditions. The present disclosure also includes methods of producing thaxtomin compounds, analogs, or intermediate with the refactored thaxtomin biosynthetic gene clusters and genetically engineered bacteria of the present disclosure.