(2S)-2,3,4,5-tetrahydrodipicolinic acid | 4226-22-6

• 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: (2S)-2,3,4,5-tetrahydrodipicolinic acid
• 英文别名: (S)-2,3,4,5-tetrahydrodipicolinic acid；(2S)-2,3,4,5-tetrahydropyridine-2,6-dicarboxylic acid
• CAS: 4226-22-6
• 化学式: C₇H₉NO₄
• 分子量: 171.153
• InChiKey: CXMBCXQHOXUCEO-BYPYZUCNSA-N

物化性质

• 沸点：
  426.0±55.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  87
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (S)-(-)-2-氨基-4-戊烯酸 在 Rh on carbon lithium hydroxide 、 三甲基氯硅烷 、 氢气 、 四氯化锡 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 69.33h， 生成 (2S)-2,3,4,5-tetrahydrodipicolinic acid
  参考文献：
  名称：

  The first stereospecific synthesis of l-tetrahydrodipicolinic acid†; a key intermediate of diaminopimelate metabolism

  摘要：

  L-四氢二吡啶羧酸1是二氨基庚二酸代谢的关键中间体，已通过6步反应从L-烯丙基甘氨酸4以23%的总产率制备得到。该合成过程中的关键步骤涉及二甲基(2RS,6S)-2-[N-(苄氧羰基)-N-(对甲苯磺酰)氨基]-6-[N-(苄氧羰基)氨基]庚烷-1,7-二酸酯8的碱介导环化反应，生成(2S)-N-(苄氧羰基)-1,2,3,4-四氢吡啶-2,6-二羧酸9。1H NMR研究表明，这一步反应涉及四个步骤：对甲苯磺酸的碱消除反应、6-苄氧羰氨基团对新生成的亚胺的分子内亲核攻击、随后酯的水解以及在酸性条件下苄氧羰胺的消除，最终得到环状烯胺9。

  DOI：

  10.1039/b105091p

文献信息

• METHOD FOR PRODUCING L-LYSINE
  申请人：DOI HIDETAKA

  公开号：US20100190217A1

  公开（公告）日：2010-07-29

  L-Lysine is produced by culturing in a medium an Escherichia coli having an L-lysine-producing ability, which has been modified to decrease the activity or activities of one or more enzymes of the meso-α,ε-diaminopimelic acid synthesis pathway, for example, 2,3,4,5-tetrahydropyridine-2,6-dicarboxylate N-succinyltransferase, succinyldiaminopimelate transaminase, succinyldiaminopimelate desuccinylase, and diaminopimelate epimerase, and into which a gene coding for diaminopimelate dehydrogenase has been introduced, and collecting L-lysine from the medium.

  L-赖氨酸是通过在培养基中培养具有L-赖氨酸生产能力的大肠杆菌生产的，该菌株已经被改造以降低中间体α,ε-二氨基戊二酸合成途径中一个或多个酶的活性，例如2,3,4,5-四氢吡啶-2,6-二羧酸N-琥珀酰转移酶、琥珀酰二氨基戊二酸转氨酶、琥珀酰二氨基戊二酸脱琥珀酰酶和二氨基戊二酸表异构酶，并且引入一个编码二氨基戊二酸脱氢酶的基因，从培养基中收集L-赖氨酸。
• Transgenic plants having increased biomass
  申请人：Ceres, Inc.

  公开号：EP2659771A1

  公开（公告）日：2013-11-06

  Methods and materials for modulating biomass levels in plants are disclosed. For example, nucleic acids encoding biomass-modulating polypeptides are disclosed as well as methods for using such nucleic acids to transform plant cells. Also disclosed are plants having increased biomass levels and plant products produced from plants having increased biomass levels.

  本文公开了调节植物生物量水平的方法和材料。例如，公开了编码生物量调节多肽的核酸以及使用这种核酸转化植物细胞的方法。还公开了生物量水平提高的植物和由生物量水平提高的植物生产的植物产品。
• Methods of increasing crop yield under abiotic stress
  申请人：CERES, INC.

  公开号：US10480000B2

  公开（公告）日：2019-11-19

  Methods and materials for increasing abiotic stress tolerance in plants are disclosed. For example, nucleic acids encoding abiotic stress tolerance-increasing polypeptides are disclosed as well as methods for using such nucleic acids to transform plant cells. Also disclosed are plants having increased tolerance to abiotic stress and methods of increasing plant yield under abiotic stress conditions.

  本文公开了提高植物非生物胁迫耐受性的方法和材料。例如，公开了编码增加非生物胁迫耐受性的多肽的核酸以及使用这种核酸转化植物细胞的方法。还公开了对非生物胁迫耐受性更强的植物以及在非生物胁迫条件下提高植物产量的方法。
• Asymmetric synthesis of differentially protected meso-2,6-diaminopimelic acid
  作者：John L. Roberts、Cecil Chan

  DOI：10.1016/s0040-4039(02)01844-0

  日期：2002.10

  meso-2,6-Diaminopimelic acid, an important linking component of bacterial cell walls and a biosynthetic precursor of L-lysine has been prepared differentially protected in a stereospecific manner from both L-aspartic and L-glutamic acid. The key step to establish the second chiral center involves the asymmetric reduction of a pyruvate moiety with Alpine-Borane(R). S-2-Amino-6-oxopimelic acid, the hydrolyzed open chain form of tetrahydrodipicolinic acid, a biosynthetic precursor of meso-2,6-diaminopimelic acid, was also prepared via deprotection of the key pyruvate intermediate. (C) 2002 Elsevier Science Ltd. All rights reserved.
• METHOD FOR PRODUCTION OF L-LYSINE
  申请人：Ajinomoto Co., Inc.

  公开号：EP2180052B1

  公开（公告）日：2013-01-23