N-carbamyl-L-isoleucine

• 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-carbamyl-L-isoleucine
• 英文别名: N-carbamoyl-L-isoleucine；(2S)-2-(carbamoylamino)-3-methylpentanoic acid
• 化学式: C₇H₁₄N₂O₃
• 分子量: 174.2
• InChiKey: AXURSAQTBIXUTE-AKGZTFGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  92.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-carbamyl-L-isoleucine 在 potassium phosphate buffer 、 Flavobacterium sp. AJ-3912 作用下， 以 various solvent(s) 为溶剂， 反应 2.0h， 生成 isoleucine
  参考文献：
  名称：

  Yokozeki, Kenzo; Hirose, Yoshiteru; Kubota, Koji, Agricultural and Biological Chemistry, 1987, vol. 51, # 3, p. 737 - 746

  摘要：

  DOI：
• 作为产物：
  描述：

  potassium cyanate 、 isoleucine 以 水 为溶剂， 反应 1.0h， 以90%的产率得到N-carbamyl-L-isoleucine
  参考文献：
  名称：

  N-单取代尿素衍生物的微波辅助合成

  摘要：

  描述了一种通过氰酸钾和多种胺之间的反应制备 N-单取代脲的简单快速的方法。该程序在微波辐射下使用水作为溶剂进行。这种方法特别有吸引力，因为它提供了高产率和纯度的尿素。

  DOI：

  10.1055/s-0030-1258553

文献信息

• Methods for producing diastereomers of isoleucine
  申请人：——

  公开号：US20040048342A1

  公开（公告）日：2004-03-11

  Methods for producing single diastereomers of isoleucine in high stereochemical purity are provided. D-isoleucine is produced by converting (R)-2-methylbutyraldehyde to a diastereomeric mixture of D-isoleucine hydantoin and L-allo-isoleucine hydantoin (5S-[(R)-1-methylpropyl]hydantoin) under conditions whereby no significant racemization of the chiral center in (R)-2-methylbutyraldehyde occurs, followed by contacting said diastereomeric hydantoin mixture with a D-hydantoinase to stereoselectively hydrolyze any D-isoleucine hydantoin in the mixture to the corresponding N-carbamoyl-D-isoleucine, preferably under conditions permitting the simultaneous epimerization of the chiral center at C-5 of the hydantoin. The simultaneous epimerization permits the reaction to be carried out to substantial completion so that the diastereomeric hydantoin mixture is converted to N-carbamoyl-D-isoleucine in high yield. The N-carbamoyl-D-isoleucine is then decarbamoylated to produce D-isoleucine. Similar procedures are used to produce single diastereomers of L-isoleucine, L-allo-isoleucine, and D-allo-isoleucine.

  提供了生产高立体化纯度的单对异构体异亮氨酸的方法。通过将(R)-2-甲基丁醛转化为D-异亮氨酸肼和L-异构异亮氨酸肼(5S-[(R)-1-甲基丙基]肼)的对映异构体混合物来生产D-异亮氨酸，条件下(R)-2-甲基丁醛手性中心没有发生显著的消旋化，然后将该对映异构体肼混合物与D-肼酶接触，以立体选择性水解混合物中的任何D-异亮氨酸肼为相应的N-氨基甲酰-D-异亮氨酸，最好在同时使肼环的C-5手性中心发生对映异构化的条件下进行。同时的对映异构化使反应可以进行到相当的完成度，以便将对映异构体肼混合物转化为高收率的N-氨基甲酰-D-异亮氨酸。然后将N-氨基甲酰-D-异亮氨酸脱氨甲酰化以产生D-异亮氨酸。类似的程序用于生产单对映异构体的L-异亮氨酸、L-异构异亮氨酸和D-异构异亮氨酸。
• DNA encoding hydantoinase, DNA encoding N-carbamyl-L-amino acid hydrolase, recombinant DNA, transformed cell, method of producing protein, and method of producing optically active amino acid
  申请人：AJINOMOTO CO. INC

  公开号：US20030109013A1

  公开（公告）日：2003-06-12

  The present invention provides a method of producing optically active amino acids from 5-substituted hydantoin by isolating a hydantoinase gene and an N-carbamyl-L-amino acid hydrolase gene involved in an ability to convert 5-substituted hydantoin or N-carbamylamino acid into optically active amino acids from a microorganism of the genus Microbacterium having the above ability and by improving gene amplification and transcriptional and translational activities thereby preparing a recombinant wherein the amount of the desired enzymes produced is increased. The hydantoinase gene is, for example, a DNA encoding for a protein having a hydantoinase activity, which has the nucleotide sequence set forth in SEQ ID NO:1 in the Sequence. The N-carbamyl-L-amino acid hydrolase gene is, for example, a DNA encoding for a protein having an N-carbamyl-L-amino acid hydrolase activity, which has the nucleotide sequence set forth in SEQ ID NO:3 in the Sequence.

  本发明提供了一种从5-取代的海因中生产光学活性氨基酸的方法，其方法是从具有上述能力的微细菌属微生物中分离出一种参与将5-取代的海因或N-氨甲酰-L-氨基酸转化为光学活性氨基酸的能力的海因酶基因和N-氨甲酰-L-氨基酸水解酶基因，并通过改进基因扩增和转录及翻译活性从而制备出一种重组体，在该重组体中所产生的所需酶的量有所增加。例如， hydantoinase 基因是编码具有 hydantoinase 活性的蛋白质的 DNA，其核苷酸序列见序列 SEQ ID NO:1 所列。例如，N-氨基甲酰-L-氨基酸水解酶基因是编码具有 N-氨基甲酰-L-氨基酸水解酶活性的蛋白质的 DNA，其核苷酸序列见序列 SEQ ID NO:3。
• DNA encoding hydantoinase, DNA encoding N-carbamyl-L-amino acid hydrolase, recombinant DNA, transformed cell, method of producing protein and method of producing optically active amino acid
  申请人：Takenaka Yasuhiro

  公开号：US20060240532A1

  公开（公告）日：2006-10-26

  The present invention provides a method of producing optically active amino acids from 5-substituted hydantoin by isolating a hydantoinase gene and an N-carbamyl-L-amino acid hydrolase gene involved in an ability to convert 5-substituted hydantoin or N-carbamylamino acid into optically active amino acids from a microorganism of the genus Microbacterium having the above ability and by improving gene amplification and transcriptional and translational activities thereby preparing a recombinant wherein the amount of the desired enzymes produced is increased. The hydantoinase gene is, for example, a DNA encoding for a protein having a hydantoinase activity, which has the nucleotide sequence set forth in SEQ ID NO:1 in the Sequence. The N-carbamyl-L-amino acid hydrolase gene is, for example, a DNA encoding for a protein having an N-carbamyl-L-amino acid hydrolase activity, which has the nucleotide sequence set forth in SEQ ID NO:3 in the Sequence.
• US6830904B2
  申请人：——

  公开号：US6830904B2

  公开（公告）日：2004-12-14
• US7098020B2
  申请人：——

  公开号：US7098020B2

  公开（公告）日：2006-08-29