D-鸟氨酸盐酸盐 | 16682-12-5

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - α-氨基酸
• 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: D-鸟氨酸盐酸盐
• 中文别名: (R)-2,5-二氨基戊酸；D-盐酸鸟氨酸；(R)-2,5-二氨基戊酸单盐酸盐；D-鸟氨酸.盐酸盐
• 英文名称: D-ornithine hydrochloride
• 英文别名: L-ornithine hydrochloride；(R)-ornithine hydrochloride；D-ornithine monohydrochloride；(2R)-2,5-diaminopentanoic acid;hydron;chloride
• CAS: 16682-12-5
• 化学式: C₅H₁₂N₂O₂*ClH
• 分子量: 168.623
• InChiKey: GGTYBZJRPHEQDG-PGMHMLKASA-N

物化性质

• 熔点：
  239 °C (dec.)(lit.)
• 比旋光度：
  [α]D20 -23.0～-24.5゜ (c=4, HCl)
• 溶解度：
  可微溶于水
• 碰撞截面：
  128.7 Ų [M-H]-; 127.9 Ų [M+H]+
• 稳定性/保质期：
  在常温常压下稳定，应避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.44
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  89.3
• 氢给体数：
  4
• 氢受体数：
  4

安全信息

• 安全说明：
  S24/25
• WGK Germany：
  3
• 海关编码：
  2922499990
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  常温密闭避光，通风干燥。

SDS

Name:	D-(-)-Ornithine hydrochloride 98% Material Safety Data Sheet
Synonym:	D-(-)-2,5-Diaminopentanoic acid hydrochloride; D-(-)-2,5-Diaminopentanoic acid; D-Ornithine, monohydrochlorid
CAS:	16682-12-5

Section 1 - Chemical Product MSDS Name:D-(-)-Ornithine hydrochloride 98% Material Safety Data Sheet
Synonym:D-(-)-2,5-Diaminopentanoic acid hydrochloride; D-(-)-2,5-Diaminopentanoic acid; D-Ornithine, monohydrochlorid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
16682-12-5	D-(-)-Ornithine hydrochloride	98	240-729-3

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: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
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:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
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 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:
Sweep up, then place into a suitable 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. 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# 16682-12-5: 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: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 239 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: > 239 deg C
Solubility in water: soluble in water
Specific Gravity/Density: Not available.
Molecular Formula: C5H12N2O2.HCl
Molecular Weight: 168.62

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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:
Oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, nitrogen.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 16682-12-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
D-(-)-Ornithine 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.
WGK (Water Danger/Protection)
CAS# 16682-12-5: 0
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 16682-12-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 16682-12-5 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

应用

鸟氨酸用于提高运动成绩、减少谷氨酰胺中毒的治疗，以及在肝脏疾病（如肝性脑病）引起的大脑条件下的支持，并有助于伤口愈合。

制备

实验中，在碱性溶液中通过一锅煮水解-消旋反应将L-精氨酸转化为DL-鸟氨酸，再利用蜂房哈夫尼菌 (Hafniaalvei AS1.1009) 中的赖氨酸脱羧酶进行生物转化，制备D-鸟氨酸盐酸盐，收率为45.3%，同时获得腐胺，收率为41.5%。研究确定，在回流条件下，以1.0 mol/L 氢氧化钠水溶液和0.10摩尔比的水杨醛催化L-精氨酸在3小时内反应可生成DL-鸟氨酸；对生物转化中的赖氨酸脱羧酶性质的研究表明，添加1 mmol/L 的 Fe2+ 可将酶活性提高至6 119 U。在此优化条件下，转化时间为16小时，为制备D-鸟氨酸盐酸盐和腐胺提供了一种新的方法。

生物活性

(R)-Ornithine hydrochloride 是一种内源性代谢产物。

反应信息

• 作为反应物：
  描述：

  D-鸟氨酸盐酸盐 在 ruthenium(IV) oxide sodium periodate 、 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 、 乙酸乙酯 、 乙腈 为溶剂， 反应 16.0h， 生成 反应停
  参考文献：
  名称：

  Suzuki, Emiko; Shibata, Norio, Enantiomer, 2001, vol. 6, # 5, p. 275 - 279

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-methyl 2-acetamido-7-chloroheptanoate 在 盐酸 作用下， 以 水 为溶剂， 反应 10.0h， 以85%的产率得到D-鸟氨酸盐酸盐
  参考文献：
  名称：

  通过不对称氢化 对非天然脂族α-氨基酸进行高度对映选择性合成†

  摘要：

  通过使用铑-双膦配合物作为催化剂，β-烷基（Z）-N-乙酰基脱氢氨基酯以高效和对映选择性的方式平稳氢化。对于一系列底物，获得了优异的对映选择性和优异的产率。还开发了一种合成口服DPP-4抑制剂类抗糖尿病药物阿格列汀和利格列汀的中间体的有效方法。

  DOI：

  10.1039/c5ob01111f

文献信息

• Pharmaceutically active ornithine derivatives, ammonium salts thereof and methods of making same
  申请人：——

  公开号：US20040072837A1

  公开（公告）日：2004-04-15

  The present invention relates to pharmaceutically active ornithine compounds, particularly to pharmaceutically acceptable ammonium salts of N &dgr; -acyl derivatives of N &agr; (4-amino-4-deoxypteroyl)-L-omithine compounds; and methods of treatment and pharmaceutical compositions that utilize or comprise one or more of such ammonium salts. The ammonium salts provided by the invention exhibit superior chemical stability than corresponding acidic N &dgr; -acyl derivatives of N &dgr; -acyl derivatives of N &agr; (4-amino-4-deoxypteroyl)-L-ornithine compounds.

  本发明涉及药用活性鸟氨酸化合物，特别是药用可接受的N &dgr; -酰基衍生物的铵盐，以及利用或包含这类铵盐的治疗方法和药物组合物。本发明提供的铵盐比相应的N &dgr; -酰基衍生物表现出更优越的化学稳定性，后者是N &agr; (4-氨基-4-脱氧叶酸)-L-鸟氨酸化合物的酸性N &dgr; -酰基衍生物。
• Methods of treating inflammatory diseases with ammonium salts of ornitihine derivatives
  申请人：Rosenwald A. Lindsay

  公开号：US20050032807A1

  公开（公告）日：2005-02-10

  The present invention relates to pharmaceutically active ornithine compounds, particularly to pharmaceutically acceptable ammonium salts of N δ -acyl derivatives of N α (4-amino-4-deoxypteroyl)-L-ornithine compounds; and methods of treatment and pharmaceutical compositions that utilize or comprise one or more of such ammonium salts. The ammonium salts provided by the invention exhibit superior chemical stability than corresponding acidic N δ -acyl derivatives of N δ -acyl derivatives of N α (4-amino-4-deoxypteroyl)-L-ornithine compounds.

  本发明涉及药用活性鸟氨酸化合物，特别是药用可接受的Nδ-酰基衍生物的Nα(4-氨基-4-脱氧叶酸)-L-鸟氨酸化合物的铵盐；以及利用或包含其中一种或多种这种铵盐的治疗方法和药物组合物。本发明提供的铵盐比相应的Nδ-酰基衍生物的Nδ-酰基衍生物的Nα(4-氨基-4-脱氧叶酸)-L-鸟氨酸化合物表现出更优越的化学稳定性。
• Structure and Reaction Mechanism of Pyrrolysine Synthase (PylD)
  作者：Felix Quitterer、Philipp Beck、Adelbert Bacher、Michael Groll

  DOI：10.1002/anie.201301164

  日期：2013.7.1

  22nd genetically encoded amino acid, pyrrolysine, is catalyzed by PylD, a structurally and mechanistically unique dehydrogenase. This catalyzed reaction includes an induced‐fit mechanism achieved by major structural rearrangements of the N‐terminal helix upon substrate binding. Different steps of the reaction trajectory are visualized by complex structures of PylD with substrate and product.

  第22种遗传编码氨基酸吡咯赖氨酸的生物合成的最后一步是由PylD催化的，PylD是一种结构上和机制上独特的脱氢酶。这种催化的反应包括诱导的拟合机制，该机制通过与底物结合时N末端螺旋的主要结构重排而实现。反应轨迹的不同步骤通过PylD与底物和产物的复杂结构可视化。
• N-carboxymethyl substituted benzolactams as inhibitors of matrix metalloproteinase
  申请人：——

  公开号：US20020095035A1

  公开（公告）日：2002-07-18

  The present invention provides a method of inhibiting matrix metallo-proteinases (MMPs) in a patient in need thereof comprising administering to the patient an effective matrix metalloproteinase inhibiting amount of the N-carboxymethyl substituted benzolactams of formula (1): 1 wherein A is —OH or —NRR′. Such inhibitors are useful in treating neoplasms, atherosclorosis, and chronic inflammatory diseases. The present invention also provides novel N-carboxymethyl substituted benzolactams of formula (1a): 2 wherein A is —NRR′.

  本发明提供了一种抑制需要患者体内基质金属蛋白酶（MMPs）的方法，包括向患者施用N-羧甲基取代苯并内酰胺的有效基质金属蛋白酶抑制剂量，其化学式为（1）： 1 其中A为—OH或—NRR′。这些抑制剂在治疗肿瘤、动脉粥样硬化和慢性炎症性疾病方面是有用的。 本发明还提供了新颖的化学式（1a）中A为—NRR′的N-羧甲基取代苯并内酰胺。
• [EN] CONJUGATES COMPRISING PEPTIDE GROUPS AND METHODS RELATED THERETO<br/>[FR] CONJUGUÉS COMPRENANT DES GROUPES PEPTIDIQUES ET PROCÉDÉS ASSOCIÉS À CEUX-CI
  申请人：LEGOCHEM BIOSCIENCES INC

  公开号：WO2017089894A1

  公开（公告）日：2017-06-01

  In some aspects, the invention relates to an antibody-drug conjugate, comprising an antibody; a linker; and at least two active agents. In preferred embodiments, the linker comprises a peptide sequence of a plurality of amino acids, and at least two of the active agents are covalently coupled to side chains of the amino acids. The antibody-drug conjugate may comprise a self-immolative group, preferably two-self-immolative groups. The linker may comprise an O-substituted oxime, e.g., wherein the oxygen atom of the oxime is substituted with a group that covalently links the oxime to the active agent; and the carbon atom of the oxime is substituted with a group that covalently links the oxime to the antibody.

  在某些方面，本发明涉及一种抗体药物偶联物，包括：抗体；连接体；以及至少两个活性剂。在优选的实施例中，连接体包括由多个氨基酸组成的肽序列，其中至少两个活性剂通过共价键与氨基酸的侧链连接。抗体药物偶联物可以包括自焚基团，优选地是两个自焚基团。连接体可以包括O-取代的肟，例如，其中肟的氧原子被取代以与活性剂形成共价键连接；肟的碳原子被取代以与抗体形成共价键连接。