(2R,3S)-(-)-2-氨基-3-羟基-4-甲基戊酸 | 87421-23-6

• 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
• 中文名称: (2R,3S)-(-)-2-氨基-3-羟基-4-甲基戊酸
• 中文别名: D(-)-苏-3-羟基亮氨酸
• 英文名称: (2R,3S)-3-hydroxyleucine
• 英文别名: (2R,3S)-2-azaniumyl-3-hydroxy-4-methylpentanoate
• CAS: 87421-23-6
• 化学式: C₆H₁₃NO₃
• 分子量: 147.174
• InChiKey: ZAYJDMWJYCTABM-UHNVWZDZSA-N

物化性质

• 熔点：
  205 °C
• 比旋光度：
  -19.4 º (c=2, 6N HCl 25 ºC)
• 沸点：
  267.28°C (rough estimate)
• 密度：
  1.2006 (rough estimate)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 安全说明：
  S24/25
• 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
• 储存条件：
  存储于0-6°C阴凉干燥处

SDS

Name:	(2R 3S)-(-)-2-Amino-3-hydroxy-4-methylpentanoic acid 99.5+% Material Safety Data Sheet
Synonym:	D(-)-threo-3-Hydroxyleucine
CAS:	87421-23-6

Section 1 - Chemical Product MSDS Name:(2R 3S)-(-)-2-Amino-3-hydroxy-4-methylpentanoic acid 99.5+% Material Safety Data Sheet
Synonym:D(-)-threo-3-Hydroxyleucine

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
87421-23-6	(2R,3S)-(-)-2-Amino-3-hydroxy-4-methyl	>99.5	unlisted

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

---

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.

---

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.
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:

---

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. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or appropriate foam.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Avoid generating dusty conditions. Provide ventilation.

---

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

---

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# 87421-23-6: 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:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystalline powder
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 206-208 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C6H13NO3
Molecular Weight: 147.17

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Dust generation, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 87421-23-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(2R,3S)-(-)-2-Amino-3-hydroxy-4-methylpentanoic acid - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

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

---

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.

---

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# 87421-23-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 87421-23-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 87421-23-6 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (2R,3S)-(-)-2-氨基-3-羟基-4-甲基戊酸 在 碳酸氢钠 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 ((2S,3R)-2-Isopropyl-4-oxo-oxetan-3-yl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Synthesis of β-chloro α-amino acids: (2S,3R)- and (2S,3S)-3-chloroleucine

  摘要：

  The first syntheses of (2S,3R)- and (2S,3S)-3-chloroleucine (3-chloro-D-leucines 1 and 2) have been achieved from D-3-hydroxyleucine and allo-D-3-hydroxyleucine, respectively, through the formation of the corresponding N-Cbz beta-lactones, followed by a ring opening promoted by lithium chloride and a debenzylation process. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.127
• 作为产物：
  描述：

  (3R,6S,3'S)-3,6-Dihydro-3-(1-hydroxy-2-methylpropyl)-6-isopropyl-2,5-dimethoxypyrazin 在 盐酸 作用下， 反应 15.0h， 生成 (2R,3S)-(-)-2-氨基-3-羟基-4-甲基戊酸
  参考文献：
  名称：

  Laxaphycins的总体结构和对肿瘤细胞增殖的抑制作用。

  摘要：

  我们从富含Lyngbya majuscula的海洋蓝细菌的混合组合中分离了一系列细胞生长抑制性环肽。通过光谱方法和降解分析确定了两种主要成分拉沙霉素A（1）和B（2）以及两种次要肽拉沙霉素B2（3）和B3（4）的结构。天然和非蛋白质氨基酸的绝对构型是通过水解，非商业残基合成，化学衍生和HPLC分析的组合来确定的。产生laxaphycins的生物被鉴定为蓝藻鱼腥藻。在一组固态和淋巴母细胞癌细胞上研究了拉沙霉素的抗增殖活性。我们的结果表明，与拉沙霉素A相比，

  DOI：

  10.1021/jm061307x

文献信息

• Cytotoxic agents and methods of use
  申请人：Xiao Xiao-Yi

  公开号：US20050203162A1

  公开（公告）日：2005-09-15

  Disclosed are compounds that inhibit proteasomic activity in cells. Also disclosed are pharmaceutical compositions comprising such compounds as well as methods to treat conditions, particularly cell proliferative conditions, such as cancer and inflammatory conditions.

  揭示了一种抑制细胞中蛋白酶体活性的化合物。还揭示了包含这些化合物的药物组合物，以及治疗疾病的方法，特别是细胞增殖性疾病，如癌症和炎症性疾病。
• Stereochemistry and Conformation of Skyllamycin, a Non-Ribosomally Synthesized Peptide from<i>Streptomyces</i>sp. Acta 2897
  作者：Vivien Schubert、Florent Di Meo、Pierre-Loïc Saaidi、Stefan Bartoschek、Hans-Peter Fiedler、Patrick Trouillas、Roderich D. Süssmuth

  DOI：10.1002/chem.201304562

  日期：2014.4.22

  Skyllamycin is a non‐ribosomally synthesized cyclic depsipeptide from Streptomyces sp. Acta 2897 that inhibits PDGF‐signaling. The peptide scaffold contains an N‐terminal cinnamoyl moiety, a β‐methylation of aspartic acid, three β‐hydroxylated amino acids and one rarely occurring α‐hydroxy glycine. With the exception of α‐hydroxy glycine, the stereochemistry of the amino acids was assigned by comparison

  Skyllamycin是来自链霉菌属的非核糖体合成的环状双缩肽。抑制PDGF信号的Acta 2897。肽支架包含一个N末端的肉桂酰基部分，一个天冬氨酸的β-甲基化，三个β-羟基化氨基酸和一个罕见的α-羟基甘氨酸。除α-羟基甘氨酸外，通过手性GC-MS和Marfey-HPLC分析将氨基酸的立体化学与合成参考氨基酸进行比较。在碱性和酸性条件下不稳定的α-羟基甘氨酸的立体化学是通过构象分析，结合NOESY-NMR光谱，模拟退火和自由MD模拟的数据确定的。模拟程序适用于R-和Skyllamycin结构的S-构型α-羟基甘氨酸，并与NOESY数据进行比较。两种方法（模拟退火和自由MD模拟）均独立支持S配置的α-羟基甘氨酸，从而实现了Skyllamycin结构中所有立体中心的分配，并将两组分黄素依赖性单加氧酶（Sky39）发挥了S选择性的作用。
• Discovery of new A- and B-type laxaphycins with synergistic anticancer activity
  作者：Weijing Cai、Susan Matthew、Qi-Yin Chen、Valerie J. Paul、Hendrik Luesch

  DOI：10.1016/j.bmc.2018.03.022

  日期：2018.5

  Two new cyclic lipopeptides termed laxaphycins B4 (1) and A2 (2) were discovered from a collection of the marine cyanobacterium Hormothamnion enteromorphoides, along with the known compound laxaphycin A. The planar structures were solved based on a combined interpretation of 1D and 2D NMR data and mass spectral data. The absolute configurations of the subunits were determined by chiral LC-MS analysis

  两种新的环状脂肽，称为拉沙霉素B4 ( 1 ) 和A2 ( 2 )，是从海洋蓝细菌Hormothamnion Enteromorphoides的集合中被发现的，以及已知的化合物拉沙霉素A。基于一维和二维核磁共振的综合解释，解析了平面结构。数据和质谱数据。通过水解产物的手性 LC-MS 分析、高级 Marfey 分析以及一维和二维 ROESY 实验确定亚基的绝对构型。与其他 laxaphycin A 型和 B 型肽的类似发现一致，laxaphycin B4 ( 1 ) 对人结肠癌 HCT116 细胞显示出抗增殖作用，IC 50为 1.7 µM，而 laxaphycin A 和 A2 ( 2 ) 则表现出较弱的活性。从样品中分离出的两种主要化合物，拉沙霉素 A 和 B4，显示出协同作用，抑制 HCT116 结直肠癌细胞的生长。
• Total Synthesis of Skyllamycins A–C
  作者：Andrew M. Giltrap、F. P. Jake Haeckl、Kenji L. Kurita、Roger G. Linington、Richard J. Payne

  DOI：10.1002/chem.201704277

  日期：2017.10.26

  skyllamycins are a family of highly functionalized non‐ribosomal cyclic depsipeptide natural products which contain the extremely rare α‐OH‐glycine functionality. Herein the first total synthesis of skyllamycins A–C is reported, together with the biofilm inhibitory activity of the natural products. Linear peptide precursors for each natural product were prepared through an efficient solid‐phase route incorporating

  Skyllamycins是一类高度功能化的非核糖体环状双缩肽天然产物，其中包含极为罕见的α-OH-甘氨酸功能。在这里，首次报道了Skyllamycins A–C的全合成，以及天然产物的生物膜抑制活性。每种天然产物的线性肽前体均通过有效的固相途径制备而成，并结合了许多合成的修饰氨基酸。在C末端酰胺和N末端乙醛酰胺部分之​​间进行的新的大环化步骤是关键的转化过程，以安装独特的α-OH-甘氨酸单元并在合成的最终步骤中生成天然产物。
• (Hetero) Bicyclymethanesulfonylamino-substituted hydroxamic acid derivatives
  申请人：——

  公开号：US20030199571A1

  公开（公告）日：2003-10-23

  Compounds of formula (I) wherein R is hydrogen, alkyl alkenyl, alkynyl, aryl, heteroaryl or heterocyclyl; and R 1 is bicyclyl or heterobicyclyl; are useful in the treatment and prophylaxis of conditions mediated by s-CD23 or TNF.

  式（I）中的化合物，其中R是氢，烷基烯基，炔基，芳基，杂芳基或杂环烷基；R1是双环烷基或杂双环烷基；在通过s-CD23或TNF介导的疾病的治疗和预防中是有用的。