5-羟基-DL-赖氨酸盐酸盐 | 13204-98-3

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 赖氨酸类衍生物
• 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
• 中文名称: 5-羟基-DL-赖氨酸盐酸盐
• 中文别名: 羟赖氨酸；盐酸-5-羟基-2,6-二氨基己酸；盐酸-DL-Δ-羟基赖氨酸；盐酸-DL-5-羟基赖氨酸；2,6-二氨基-5-羟基己酸盐酸盐；DL-plusallo-δ-羟赖氨酸合氯化氢；DL-PLUSALLO-Δ-羟赖氨酸合氯化氢；DL-5-羟基赖氨酸盐酸盐
• 英文名称: 5-hydroxylysine hydrochloride
• 英文别名: DL-5-hydroxylysine hydrochloride；2,6-Bis(azaniumyl)-5-hydroxyhexanoate;chloride；2,6-bis(azaniumyl)-5-hydroxyhexanoate;chloride
• CAS: 13204-98-3
• 化学式: C₆H₁₄N₂O₃*ClH
• 分子量: 198.65
• InChiKey: MJXVOTKVFFAZQJ-UHFFFAOYSA-N

物化性质

• 熔点：
  225 °C (dec.)(lit.)
• 比旋光度：
  [α]D20 -0.5～+0.5°(c=5,H2O)
• 溶解度：
  甲醇（微溶）、水（微溶）
• 碰撞截面：
  134.2 Ų [M-H]-; 135 Ų [M+H]+; 137.7 Ų [M+Na]+

计算性质

• 辛醇/水分配系数(LogP)：
  -1.08
• 重原子数：
  12
• 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：
  5
• 氢受体数：
  5

安全信息

• 安全说明：
  S24/25
• WGK Germany：
  3
• 海关编码：
  2922509090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Name:	5-Hydroxy-DL-lysine hydrochloride Material Safety Data Sheet
Synonym:	DL-Lysine, 5-hydroxy-, monohydrochloride; 2,6-Diamino-5-hydroxycaproic acid hydrochlorid
CAS:	13204-98-3

Section 1 - Chemical Product MSDS Name:5-Hydroxy-DL-lysine hydrochloride Material Safety Data Sheet
Synonym:DL-Lysine, 5-hydroxy-, monohydrochloride; 2,6-Diamino-5-hydroxycaproic acid hydrochlorid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
13204-98-3	5-Hydroxy-DL-lysine hydrochloride	100	236-168-9

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 13204-98-3: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 225.00 - 227.00 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C6H14N2O3.HCl
Molecular Weight: 198.65

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, strong oxidants.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 13204-98-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
5-Hydroxy-DL-lysine hydrochloride - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 13204-98-3: No information available.
Canada
CAS# 13204-98-3 is listed on Canada's NDSL List.
CAS# 13204-98-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 13204-98-3 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性方面，DL-5-羟基赖氨酸盐酸盐是一种内源性代谢产物，由D-和L-对映体组成，可作为自由基诱导的蛋白质氧化的潜在靶点。

反应信息

• 作为反应物：
  描述：

  5-羟基-DL-赖氨酸盐酸盐 在 sodium periodate 、 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 0.13h， 生成 L-1-pyrroline-5-carboxylic acid
  参考文献：
  名称：

  比较和综合代谢组学表明，S-亚硝化抑制生理相关的代谢酶。

  摘要：

  半胱氨酸 S-亚硝化是由一氧化氮 (•NO) 衍生试剂介导的可逆翻译后修饰。S-亚硝化参与细胞信号传导并与多种疾病相关，例如癌症、心血管疾病和神经元疾病。尽管这种非经典的•NO 信号通路在生理上具有重要意义，但人们对 S-亚硝化对蛋白质功能的影响程度知之甚少。此外，由于转亚硝化的动力学和对导致选择性蛋白质 S-亚硝化的生理机制的了解有限，鉴定 S-亚硝化的生理相关靶标是困难的。为了鉴定活性受 S-亚硝化调节的蛋白质，我们进行了一项代谢组学研究，比较了 WT 和内皮一氧化氮合酶敲除小鼠。我们将我们的结果与先前确定生理相关 S-亚硝化半胱氨酸的蛋白质组学研究的结果相结合，我们发现至少 21 种代谢酶的活性可能受到 S-亚硝化的调节。我们克隆、表达和纯化了其中四种酶，并观察到 ​​S-亚硝化抑制代谢酶 6-磷酸葡萄糖酸脱氢酶、Δ1-吡咯啉-5-羧酸脱氢酶、儿茶酚-O-甲基转移酶和 d-3-磷酸甘

  DOI：

  10.1074/jbc.m117.817700

文献信息

• [EN] INHIBITORS OF INDOLEAMINE 2,3-DIOXYGENASE AND/OR TRYPTOPHAN 2,3-DIOXYGENASE<br/>[FR] INHIBTEURS DE L'INDOLÉAMINE 2,3-DIOXYGÉNASE ET/OU DU TRYPTOPHANE DIOXYGÉNASE
  申请人：IDORSIA PHARMACEUTICALS LTD

  公开号：WO2019034725A1

  公开（公告）日：2019-02-21

  The present invention relates to compounds of Formula (I) inhibiting indoleamine 2,3-dioxygenase (IDO) and/or tryptophan 2,3-dioxygenase (TDO) enzymes. Further, their synthesis and their use as medicaments in inter alia cancer is disclosed.

  这项发明涉及抑制吲哚胺 2,3-二氧化酶（IDO）和/或色氨酸 2,3-二氧化酶（TDO）酶的化合物（I）的公式。此外，还披露了它们的合成以及它们在包括癌症在内的药物中的用途。
• [EN] BIOSYNTHETICALLY GENERATED PYRROLINE-CARBOXY-LYSINE AND SITE SPECIFIC PROTEIN MODIFICATIONS VIA CHEMICAL DERIVATIZATION OF PYRROLINE-CARBOXY-LYSINE AND PYRROLYSINE RESIDUES<br/>[FR] PYRROLINE-CARBOXY-LYSINE PRODUITE PAR BIOSYNTHÈSE ET MODIFICATIONS DE PROTÉINES SPÉCIFIQUES DE SITE OBTENUES PAR UNE DÉRIVATISATION CHIMIQUE DE PYRROLINE-CARBOXY-LYSINE ET DE RÉSIDUS DE PYRROLYSINE
  申请人：IRM LLC

  公开号：WO2010048582A1

  公开（公告）日：2010-04-29

  Disclosed herein is pyrroline-carboxy-lysine (PCL), a pyrrolysine analogue, which is a natural, biosynthetically generated amino acid, and methods for biosynthetically generating PCL. Also disclosed herein are proteins, polypeptides and peptides that have PCL incorporated therein and methods for incorporating PCL into such proteins, polypeptides and peptides. Also disclosed herein is the site-specific derivatization of proteins, polypeptides and peptides having PCL or pyrrolysine incorporated therein. Also disclosed herein is the crosslinking of proteins, polypeptides and peptides having PCL or pyrrolysine incorporated therein.

  本文披露了吡咯酮羧基赖氨酸（PCL），一种吡咯赖氨酸类似物，它是一种天然的、生物合成产生的氨基酸，以及生物合成生成PCL的方法。本文还披露了含有PCL的蛋白质、多肽和肽以及将PCL纳入这些蛋白质、多肽和肽中的方法。本文还披露了具有PCL或吡咯赖氨酸的蛋白质、多肽和肽的特定位点衍生化。本文还披露了具有PCL或吡咯赖氨酸的蛋白质、多肽和肽的交联。
• Traceless and Site-Specific Ubiquitination of Recombinant Proteins
  作者：Satpal Virdee、Prashant B. Kapadnis、Thomas Elliott、Kathrin Lang、Julia Madrzak、Duy P. Nguyen、Lutz Riechmann、Jason W. Chin

  DOI：10.1021/ja202799r

  日期：2011.7.20

  Protein ubiquitination is a post-translational modification that regulates almost all aspects of eukaryotic biology. Here we discover the first routes for the efficient site-specific incorporation of δ-thiol-l-lysine (7) and δ-hydroxy-l-lysine (8) into recombinant proteins, via evolution of a pyrrolysyl-tRNA synthetase/tRNACUA pair. We combine the genetically directed incorporation of 7 with native

  蛋白质泛素化是一种翻译后修饰，可调节真核生物学的几乎所有方面。在这里，我们发现了通过吡咯赖氨酰-tRNA 合成酶/tRNACUA 对的进化，将 δ-硫醇-l-赖氨酸 (7) 和 δ-羟基-l-赖氨酸 (8) 有效位点特异性掺入重组蛋白的第一条途径. 我们将 7 的遗传定向掺入与天然化学连接和脱硫相结合，以在底物蛋白和泛素之间产生完全天然的异肽键。我们通过展示泛素二聚体的合成和泛素化 SUMO 的首次合成来举例说明这种方法。
• Model studies towards prodrugs of the glutamine antagonist 6-diazo-5-oxo-l-norleucine (DON) containing a diazo precursor
  作者：Run-Duo Gao、Niyada Hin、Eva Prchalová、Arindom Pal、Jenny Lam、Rana Rais、Barbara S. Slusher、Takashi Tsukamoto

  DOI：10.1016/j.bmcl.2021.128321

  日期：2021.10

  2-acetamido-6-(((benzyloxy)carbonyl)(nitroso)amino)-5-oxohexanoic acid (5) containing a N-nitrosocarbamate group, which can be converted to a diazo moiety via a mechanism similar to that of streptozotocin, a clinically approved diazomethane-releasing drug containing an N-nitrosourea group. Preliminary characterization confirmed formation of N-acetyl DON (6), also known as duazomycin A, from compound 4

  在设计谷氨酰胺拮抗剂 6-diazo-5-oxo-l-norleucine (DON) 的前药时，探索了两种不同的重氮前体，即咪唑四嗪和亚硝胺。作为基于咪唑四嗪的前药模型，我们合成了 ( S )-2-acetamido-6-(8-carbamoyl-4-oxoimidazo[5,1- d ][1,2,3,5]tetrazin-3( 4 H )-yl)-5-oxohexanoic acid ( 4 ) 包含替莫唑胺的整个支架，替莫唑胺是临床上批准用于治疗多形性胶质母细胞瘤的 DNA 甲基化剂的前体。对于基于亚硝酰胺的前药，我们合成了含有N-亚硝基氨基甲酸酯基团，可通过类似于链脲佐菌素的机制转化为重氮基团，链脲佐菌素是一种临床批准的含有N-亚硝基脲基团的重氮甲烷释放药物。初步表征证实了从化合物4以 pH 依赖性方式形成N-乙酰 DON ( 6)，也称为 duazomycin A，而化合物5没有
• LYSINE COMPOUNDS AND THEIR USE IN SITE- AND CHEMOSELECTIVE MODIFICATION OF PEPTIDES AND PROTEINS
  申请人：Ovaa Huib

  公开号：US20120135913A1

  公开（公告）日：2012-05-31

  The present invention concerns new thiolysine and selenolysine compounds that can be used as building blocks for peptides and proteins, providing ligation handles for site- and chemoselective modification of said peptides and proteins. In particular, the invention provides. In particular, the invention provides (the use of) the compounds 5-thiolysine (also referred to as δ-thiolysine); 4-thiolysine (also referred to as γ-thiolysine); 5-selenolysine (also referred to as δ-selenolysine) and 4-selenolysine (also referred to as γ-selenolysine). The positioning of the thiol or selenol group at the respective carbon atom allows for a very efficient intramolecular transfer reaction to take place after conjugation with a selected ligand, and the thiol or selenol group may subsequently be removed using reported procedures, thereby restoring the native lysine structure, or be used as an additional conjugation handle. The methodology is fast and gives well-defined material.

  本发明涉及新的巯基赖氨酸和硒基赖氨酸化合物，可用作肽和蛋白质的构建块，为所述肽和蛋白质的位点和化学选择性修饰提供连接手柄。具体而言，本发明提供了化合物5-巯基赖氨酸（也称为δ-巯基赖氨酸）；4-巯基赖氨酸（也称为γ-巯基赖氨酸）；5-硒基赖氨酸（也称为δ-硒基赖氨酸）和4-硒基赖氨酸（也称为γ-硒基赖氨酸）的使用。将巯基或硒基团位于相应的碳原子上，可在与所选配体共轭后发生非常高效的分子内转移反应，巯基或硒基团随后可使用已知的程序去除，从而恢复天然的赖氨酸结构，或用作额外的连接手柄。该方法快速且给出明确的材料。