(2S,5S)-5-hydroxylysine | 18899-29-1

• 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: (2S,5S)-5-hydroxylysine
• 英文别名: 5S-hydroxy-L-lysine；L_S-threo-5-hydroxy-lysine；L_S-threo-2,6-Diamino-5-hydroxy-hexansaeure；L_S-threo-5-Hydroxy-lysin；DL-Allohydroxy-lysin；(2S,5S)-2,6-diamino-5-hydroxyhexanoic acid
• CAS: 18899-29-1
• 化学式: C₆H₁₄N₂O₃
• 分子量: 162.189
• InChiKey: YSMODUONRAFBET-WHFBIAKZSA-N

物化性质

• 沸点：
  416.2±45.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  110
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  硫代异氰酸苯酯 、 (2S,5S)-5-hydroxylysine 生成 (2S,5S)-5-hydroxy-2,6-bis(phenylcarbamothioylamino)hexanoic acid
  参考文献：
  名称：

  DAVEY, JOHN F.;ERSSER, ROGER S., J. CHROMATOGR. BIOMED. APPL.,(1990) N28, 1, C. 9-23

  摘要：

  DOI：
• 作为产物：
  描述：

  Α-D-乳酸吡喃糖苷甲酯 在 吡啶 、 sodium azide 、 palladium 10% on activated carbon 、 氢气 、 sodium methylate 、 氢氧化锆 、 silica gel 、 对甲苯磺酸 、 pyridinium chlorochromate 、 原甲酸三甲酯 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， -50.0~135.0 ℃ 、101.33 kPa 条件下， 反应 120.0h， 生成 (2S,5S)-5-hydroxylysine
  参考文献：
  名称：

  从d-半乳糖作为手性前体 轻松合成5-羟基-1-赖氨酸†

  摘要：

  通过利用D-半乳糖作为具有立体保留性的手性前体，可以实现（2 S，5 R）和（2 S，5 S）-5-羟基赖氨酸的简明合成。这种合成策略展示了利用碳水化合物作为起始原料制备氨基酸的潜力。使用二叠氮中间体，合成了衍生的β- D-吡喃半乳糖基和α- D-吡喃葡萄糖基- （1→2）-β- D-半乳糖基部分。

  DOI：

  10.1039/c4ob01220h

文献信息

• Stereoselective preparation of cyclic l-amino acids
  申请人：Thibaut Denis

  公开号：US20050038255A1

  公开（公告）日：2005-02-17

  The invention concerns a method for producing a cyclic L-amino acid of formula (I), characterised in that it consists in reacting a L-diamino acid of formula (II) or an enantiomeric mixture comprising such a L-diamino acid and a corresponding D-diamino acid in variable proportions, in the presence of an ornithine cyclodeaminase or a polypeptide homologous to the ornithine cyclodeaminase.

  该发明涉及一种生产式（I）的环状L-氨基酸的方法，其特征在于在鸟氨酸环脱氨酶或与鸟氨酸环脱氨酶同源的多肽存在下，通过反应式（II）的L-二氨基酸或包含这样的L-二氨基酸和相应的D-二氨基酸的对映体混合物，以可变比例进行反应。
• The 2-Oxoglutarate-Dependent Oxygenase JMJD6 Catalyses Oxidation of Lysine Residues to give 5S-Hydroxylysine Residues
  作者：Monica Mantri、Nikita D. Loik、Refaat B. Hamed、Timothy D. W. Claridge、James S. O. McCullagh、Christopher J. Schofield

  DOI：10.1002/cbic.201000641

  日期：2011.3.7

  Amino acid analyses reveal that JMJD6‐catalysed hydroxylation of RNA‐splicing regulatory protein fragments occurs to give hydroxylysine products with 5S stereochemistry. This contrasts with collagen lysyl hydroxylases, which give 5R‐hydroxylated products. The work suggests that more than one subfamily of lysyl hydroxylases has evolved and illustrates the importance of stereochemical assignments in

  氨基酸分析表明，JMJD6 催化的 RNA 剪接调节蛋白片段的羟基化产生具有 5 S立体化学的羟基赖氨酸产物。这与胶原蛋白赖氨酰羟化酶形成对比，后者产生 5 R-羟基化产物。这项工作表明，已经进化出不止一个赖氨酰羟化酶亚家族，并说明了立体化学分配在蛋白质组学分析中的重要性。
• New enzymes and method for preparing hydroxylated L-lysine or L-ornithine and analogs thereof
  申请人：COMMISSARIAT A L'ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES

  公开号：EP2876156A1

  公开（公告）日：2015-05-27

  The present invention relates to new enzymes displaying L-lysine or L-ornithine hydroxylase activity and their uses for preparing compounds of interest, in particular hydroxy-L-lysine, hydroxy-L-ornithine and hydroxylated diamino alkanes.

  本发明涉及显示 L-赖氨酸或 L-鸟氨酸羟化酶活性的新酶及其用于制备相关化合物的用途，特别是羟基-L-赖氨酸、羟基-L-鸟氨酸和羟基化二氨基烷烃。
• 3-Hydroxylysine, a Potential Marker for Studying Radical-Induced Protein Oxidation
  作者：Bénédicte Morin、William A. Bubb、Michael J. Davies、Roger T. Dean、Shanlin Fu

  DOI：10.1021/tx980118h

  日期：1998.11.1

  gamma-Irradiation of several amino acids (Val, Leu, lie, Lys, Pro, and Glu) in the presence of O-2 generates hydroperoxides. We have previously isolated and characterized valine and leucine hydroperoxides, and hydroxides, and have detected these products in both isolated systems [e.g., bovine serum albumin (BSA) and human low-density lipoprotein (LDL)] and diseased human tissues (atherosclerotic plaques and lens cataractous proteins). This work was aimed at investigating oxidized lysine as a sensitive marker for protein oxidation, as such residues are present on protein surfaces, and are therefore likely to be particularly susceptible to oxidation by radicals in bulk solution. HO. attack on lysine in the presence of oxygen, followed by NaBH4 reduction, is shown to give rise to (2S)-3-hydroxylysine [(2S)-2,6-diamino-3-hydroxyhexanoic acid], (2S)-4-hydroxylysine [(2S)-2,6-diamino-4-hydroxyhexanoic acid], (2S,5R)-5-hydroxylysine [(2S,5R)-2,6-diamino-5-hydroxyhexanoic acid], and (2S,5S)-5-hydroxylysine [(2S,5S)-2,6-diamino-5-hydroxyhexanoic acid]. 5-Hydroxylysines are natural products formed by lysyl oxidase and are therefore not good markers of radical-mediated oxidation. The other hydroxylysines are however useful markers, with HPLC analysis of 9-fluorenylmethyl chloroformate (FMOC) derivatives providing a sensitive and accurate method for quantitative measurement. Hydroxylysines have been detected in the hydrolysates of peptides (Gly-Lys-Gly and Lys-Val-Ile-Leu-Phe) and proteins (BSA and histone H1) exposed to HO ./O-2, and subsequently treated with NaBH4. Quantification of the hydroxylysines yields, and comparison with hydroxyvalines and hydroxyleucines, supports the hypothesis that surface residues give higher yields of oxidized products than the hydrophobic leucines and valines, at least with globular proteins such as BSA. Hydroxylysines, and particularly 3-hydroxylysine, may therefore be sensitive and useful markers of radical-mediated protein oxidation in biological systems.
• Synthesis of all four possible stereoisomers of 5-hydroxylysine
  作者：Pietro Allevi、Mario Anastasia

  DOI：10.1016/s0957-4166(00)00281-0

  日期：2000.8

  A simple protocol for the transformation of L- and D-glutamic acids into the enantiopure forms of all four isomers of 5-hydroxylysine is described. (C) 2000 Elsevier Science Ltd. All rights reserved.