Z-D-正缬氨酸 | 42918-89-8

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 缬氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: Z-D-正缬氨酸
• 英文名称: N-(benzyloxycarbonyl)-D-norvaline
• 英文别名: Z-D-Nva-OH；(2R)-2-(phenylmethoxycarbonylamino)pentanoic acid
• CAS: 42918-89-8
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: NSJDRLWFFAWSFP-LLVKDONJSA-N

物化性质

• 熔点：
  89.5-90℃ (ethyl acetate ligroine )
• 沸点：
  439.4±38.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090
• 储存条件：
  存储条件：0-5°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Z-D-Nva-OH
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: Z-D-Nva-OH
CAS number: 42918-89-8

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C13H17NO4
Molecular weight: 251.3

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  Z-D-正缬氨酸 在 氢氧化钾 、 二异丁基氢化铝 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 3.0h， 生成 (R)-N-Cbz-丙基甘氨醛
  参考文献：
  名称：

  pamamycin-607的总合成。第2部分：C6-C18域的合成

  摘要：

  帕马霉素-607的C6-C18结构域的合成可通过十个步骤完成，而市售d-正缬氨酸的总产率为7％。关键的不对称转化包括Paterson抗羟醛加成，所得β-羟基酮的抗选择性还原和顺式选择性Bartlett型环闭合。

  DOI：

  10.1016/j.tet.2006.01.005
• 作为产物：
  描述：

  N-benzyloxycarbonyl-D-norvaline 2,2,2-trifluoroethyl ester 在 sodium hydroxide 作用下， 以410 mg的产率得到Z-D-正缬氨酸
  参考文献：
  名称：

  Resolution of non-proteinogenic amino acids via microbial lipase-catalyzed enantioselective transesterification

  摘要：

  通过伯克霍尔德氏菌脂肪酶催化的2,2,2-三氟乙基酯的对映体选择性酯化反应，在二异丙基醚中以甲醇为亲核体，分离出了一些带有脂肪族侧链的非蛋白源氨基酸，其对映体选择性为中等到良好（E = 15-42）。关键词：非蛋白源氨基酸；微生物脂肪酶；伯克霍尔德氏菌脂肪酶；2,2,2-三氟乙基酯；对映选择性酯交换反应；对映选择性。

  DOI：

  10.1139/v07-154

文献信息

• Enantioselective inclusion of pyrene-1-sulfonate salts of α-amino acids with crystals of α-cyclodextrin
  作者：Ikuko Miyoshi、Yuichi Kitamoto、Tetsuya Maeda、Naoya Morohashi、Tetsutaro Hattori

  DOI：10.1016/j.tet.2020.131100

  日期：2020.4

  Enantioselective inclusion of α-amino acids with crystals of α-cyclodextrin (α-CD) has been achieved by converting the amino acids into sulfonate salts with pyrene-1-sulfonic acid (PyS). For example, crystals of α-CD selectively include l-leucine/PyS (1:1) salt in a host/guest ratio of ∼1 with 92%ee from a solution of the racemic salt in ethanol/N-methylformamide (91:9) at 40 °C. Under conditions optimized

  的对映选择性包含α -氨基羧酸与晶体α环糊精（α -CD）已经由氨基酸转化成磺酸盐与芘-1-磺酸（PYS）来实现的。例如，α -CD的晶体选择性地含有约1的主体/客体比率的1-亮氨酸/ PyS（1：1）盐和来自消旋盐的乙醇/ N溶液的92％ee-甲基甲酰胺（91：9）在40°C下。在针对单个氨基酸优化的条件下，缬氨酸，苯丙氨酸和蛋氨酸的PyS盐也具有良好的对映选择性（最高86％ee）。对亮氨酸/ PyS盐包合物的机理研究表明，对映选择性源于D和1-亮氨酸/ PyS盐与α -CD包合物在晶体中稳定性的差异。
• Optical resolution of unusual amino–acids by lipase-catalysed hydrolysis
  作者：Toshifumi Miyazawa、Tadanori Takitani、Shinichi Ueji、Takashi Yamada、Shigeru Kuwata

  DOI：10.1039/c39880001214

  日期：——

  The 2-chloroethyl esters of the N-benzyloxycarbonyl (Z) derivatives of several unusual amino-acids are converted by Aspergillus niger lipase into enantiomerically enriched Z-amino-acids with fairly high optical purities, the L-enantiomers being preferentially hydrolysed.

  黑曲霉脂肪酶将几种不同氨基酸的N-苄氧基羰基（Z）衍生物的2-氯乙基酯转化为对映异构体富集的Z-氨基酸，具有相当高的光学纯度，L-对映体优先水解。
• Direct Optical Resolution of Carboxylic Acids by Chiral HPLC on Tris(3,5-dimethylphenylcarbamate)s of Cellulose and Amylose
  作者：Yoshio Okamoto、Ryo Aburatani、Yuriko Kaida、Koichi Hatada

  DOI：10.1246/cl.1988.1125

  日期：1988.7.5

  A variety of racemic carboxylic acids have been for the first time directly resolved by normal-phase, high-performance liquid chromatography using a hexane-2-propanol eluting system containing a small amount (≈1%) of a strong carboxylic acid, like formic acid, trichloroacetic acid, and trifluoroacetic acid.

  多种外消旋羧酸首次通过正相高效液相色谱法直接拆分，该方法采用含有少量（约1%）强羧酸（如甲酸、三氯乙酸和三氟乙酸）的己烷-2-丙醇洗脱系统。
• Primary Amino Acid Derivatives: Compounds with Anticonvulsant and Neuropathic Pain Protection Activities
  作者：Amber M. King、Christophe Salomé、Jason Dinsmore、Elise Salomé-Grosjean、Marc De Ryck、Rafal Kaminski、Anne Valade、Harold Kohn

  DOI：10.1021/jm2004305

  日期：2011.7.14

  R-substituent was varied, including C(2) stereochemistry, and the compounds were tested in rodent models of seizures and neuropathic pain. C(2)-Hydrocarbon N-benzylamide PAADs were potent anticonvulsants and excellent anticonvulsant activity (mice, ip; rat, po) was observed for C(2) R-substituted PAADs in which the R group was ethyl, isopropyl, or tert-butyl, and the C(2) stereochemistry conformed to the

  药理管理仍然是治疗癫痫和神经性疼痛的主要方法。我们已经开发了一种称为功能化氨基酸（FAA）的新型抗惊厥药。在这项研究中，我们研究了从末端乙酰基部分被除去的FAA衍生物，并将其称为这些化合物伯氨基酸衍生物（PAAD）。编写了27个PAAD。中央C（2）R取代基是多样的，包括C（2）立体化学，和化合物在癫痫发作和神经性疼痛的啮齿动物模型中进行了测试。C（2） -烃Ñ -苄基酰胺PAADs是有效的抗惊厥药和优异的抗惊厥活性（小鼠，腹膜内;大鼠，口服）观察到C（2）R-取代PAADs其中R基团是乙基，异丙基，或叔-丁基和C（2）立体化学符合d-氨基酸构型（（R）-立体异构体）。这些值超过了几种临床抗癫痫药的活性。C（2）（R）-乙基和C（2）（R）-异丙基PAADs在小鼠（ip）福尔马林神经性疼痛模型中也显示出出色的活性。值得注意的是，与FAA结构-活性关系不同，PAAD抗惊厥活性在亚甲基单元取代
• Structure-Activity Study of 5-Substituted 1-Carbobenzoxy-2-iminohydantoins as Potential Anticonvulsant Agents
  作者：Zhong-Yue Sun、Chul-Hoon Kwon、John N. D. Wurpel

  DOI：10.1021/jm00044a003

  日期：1994.9

  compounds except 8 also showed activity against the scMET test with ED50 values in the range of 141-223 mg/kg. All significantly active compounds (1, 6, 7a, 8, 9, and 11) possessed aliphatic hydrocarbon side chains of two- to three-carbon lengths at the C5 position. All of the compounds with no or minimal activity had either shorter or longer side chains. The compounds substituted at the C5 position by

  根据我们先前的发现，已合成了一系列5取代的2-亚氨基乙内酰脲并进行了抗惊厥活性试验，以更好地了解2-亚氨基乙内酰脲的SAR。在测试的化合物中，（S）-（+）-1-碳-苄氧基-2-亚氨基乙内酰脲类似物与乙基（6）-，正丙基（7a）-，异丙基（8）-，烯丙基（9）-和仲亚氨基乙内酰脲环的C5上的丁基（11）取代基提供的抗MES试验的最佳活性，ED50值在52-74 mg / kg的范围内。除8种化合物外，所有上述化合物均显示出抗scMET试验的活性，ED50值在141-223 mg / kg范围内。所有显着活性的化合物（1、6、7a，8、9和11）在C5位置均具有2至3个碳原子长度的脂族烃侧链。所有没有或仅有最小活性的化合物具有较短或较长的侧链。在C5位置被芳基，芳基烷基或含有杂原子的烷基和芳基烷基取代的化合物也没有显示出对MES和scMET测试的活性。结果表明，当2-亚氨基乙内酰脲具有正确的