苄氧羰基-L-脯氨酸 4-硝基苯基酯 | 3304-59-4

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 脯氨酸类衍生物
• 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: 苄氧羰基-L-脯氨酸 4-硝基苯基酯
• 中文别名: 苄氧羰基-L-脯氨酸4-硝基苯基酯；苄氧基羰基-l-脯氨酸-4-硝基苯酯；Cbz-L-脯氨酸-4-硝基苯酯
• 英文名称: N-benzyloxycarbonyl-L-proline p-nitrophenyl ester
• 英文别名: (2S)-N-benzyloxycarbonyl-(4-nitrophenyl) pyrrolidine-2-carboxylate；1-benzyl 2-(4-nitrophenyl) (S)-pyrrolidine-1,2-dicarboxylate；N-carbobenzoxy-(S)-proline-p-nitrophenol ester；N-carbobenzoxy-DL-proline p-nitrophenyl ester；1-benzyloxycarbonyl-L-proline-(4-nitro-phenyl ester)；1-Benzyloxycarbonyl-L-prolin-(4-nitro-phenylester)；benzyloxycarbonyl-L-proline p-nitrophenyl ester；N-CBZ-L-proline 4-nitrophenyl ester；Z-Pro-ONp；1-O-benzyl 2-O-(4-nitrophenyl) (2S)-pyrrolidine-1,2-dicarboxylate
• CAS: 3304-59-4
• 化学式: C₁₉H₁₈N₂O₆
• mdl: MFCD00020828
• 分子量: 370.362
• InChiKey: GXUFIJVKXYWCAO-KRWDZBQOSA-N

物化性质

• 熔点：
  94-95.5 °C
• 沸点：
  541.7±50.0 °C(Predicted)
• 密度：
  1.356±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.263
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P280
• 危险性描述：
  H302,H317
• 储存条件：
  2-8°C

SDS

Version 1.2
Regulation (EC) No 1907/2006

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1 - Product and Company Information

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Product Name N-CBZ-L-PROLINE P-NITROPHENYL ESTER
CRYSTALLINE

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2 - Hazards Identification

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3 - Composition/Information on Ingredients

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Product Name CAS # EC no Annex I
Index Number
N-CBZ-L-PROLINE P-NITROPHENYL 3304-59-4 221-981-3 None
ESTERCRYSTALLINE
Formula C19H18N2O6
Molecular Weight 370,4000 AMU
Synonyms 1-Benzyl p-nitrophenyl
L-1,2-pyrrolidinedicarboxylate *
Carbobenzyloxy-L-proline p-nitrophenyl ester *
L-Proline, carbobenzyloxy-, p-nitrophenyl ester

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4 - First Aid Measures

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AFTER INHALATION
If inhaled, remove to fresh air. If breathing becomes difficult,
call a physician.
AFTER SKIN CONTACT
In case of skin contact, flush with copious amounts of water for
at least 15 minutes. Remove contaminated clothing and shoes.
Call a physician.
AFTER EYE CONTACT
In case of contact with eyes, flush with copious amounts of
water for at least 15 minutes. Assure adequate flushing by
separating the eyelids with fingers. Call a physician.
AFTER INGESTION
If swallowed, wash out mouth with water provided person is
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conscious. Call a physician.

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5 - Fire Fighting Measures

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EXTINGUISHING MEDIA
Suitable: Water spray. Carbon dioxide, dry chemical powder, or
appropriate foam.
SPECIAL RISKS
Specific Hazard(s): Emits toxic fumes under fire conditions.
SPECIAL PROTECTIVE EQUIPMENT FOR FIREFIGHTERS
Wear self-contained breathing apparatus and protective clothing
to prevent contact with skin and eyes.

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6 - Accidental Release Measures

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PROCEDURE(S) OF PERSONAL PRECAUTION(S)
Wear protective equipment.
METHODS FOR CLEANING UP
Sweep up, place in a bag and hold for waste disposal. Avoid
raising dust. Ventilate area and wash spill site after material
pickup is complete.

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7 - Handling and Storage

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STORAGE
Store at 2-8°C

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8 - Exposure Controls / Personal Protection

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ENGINEERING CONTROLS
Mechanical exhaust required.
PERSONAL PROTECTIVE EQUIPMENT
Special Protective Measures: Wear appropriate government approved
respirator, chemical-resistant gloves, safety goggles, other
protective clothing.

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9 - Physical and Chemical Properties

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Appearance Physical State: Solid
Property Value At Temperature or Pressure
pH N/A
BP/BP Range N/A
MP/MP Range N/A
Flash Point N/A
Flammability N/A
Autoignition Temp N/A
Oxidizing Properties N/A
Explosive Properties N/A
Explosion Limits N/A
Vapor Pressure N/A
Partition Coefficient N/A
Viscosity N/A
Vapor Density N/A
Saturated Vapor Conc. N/A
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Evaporation Rate N/A
Bulk Density N/A
Decomposition Temp. N/A
Solvent Content N/A
Water Content N/A
Surface Tension N/A
Conductivity N/A
Miscellaneous Data N/A
Solubility N/A

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10 - Stability and Reactivity

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STABILITY
Stable: Stable.
HAZARDOUS DECOMPOSITION PRODUCTS
Hazardous Decomposition Products: Carbon monoxide, Carbon dioxide,
Nitrogen oxides.
HAZARDOUS POLYMERIZATION
Hazardous Polymerization: Will not occur

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11 - Toxicological Information

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RTECS NUMBER: UY0750000
ACUTE TOXICITY
LD50
Intravenous
Mouse
320 MG/KG
ROUTE OF EXPOSURE
Multiple Routes: May cause irritation. May be harmful by
inhalation, ingestion, or skin absorption.
CONDITIONS AGGRAVATED BY EXPOSURE
The toxicological properties have not been thoroughly
investigated.

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12 - Ecological Information

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No data available.

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13 - Disposal Considerations

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SUBSTANCE DISPOSAL
Dissolve or mix the material with a combustible solvent and burn
in a chemical incinerator equipped with an afterburner and
scrubber. Observe all federal, state, and local environmental
regulations.

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14 - Transport Information

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RID/ADR
Non-hazardous for road transport.
IMDG
Non-hazardous for sea transport.
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IATA
Non-hazardous for air transport.

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15 - Regulatory Information

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COUNTRY SPECIFIC INFORMATION
Germany
WGK: 3
Self-Classification

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16 - Other Information

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WARRANTY
The above information is believed to be correct but does not
purport to be all inclusive and shall be used only as a guide. The
information in this document is based on the present state of our
knowledge and is applicable to the product with regard to
appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Inc.,
shall not be held liable for any damage resulting from handling or
from contact with the above product. See reverse side of invoice
or packing slip for additional terms and conditions of sale.
Copyright 2010 Co. License granted to make
unlimitedpaper copies for internal use only.
DISCLAIMER
For R&D use only. Not for drug, household or other uses.
SIGMA www.molbase.com

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  苄氧羰基-L-脯氨酸 4-硝基苯基酯 在 氢气 作用下， 生成 PG-NH2
  参考文献：
  名称：

  Luliberin及其类似物的合成方案

  摘要：

  WillardineB3°-（人胰岛素）的甲酯（II）。Rf 0.51 (CsHsN--C4HgOH--CH3CO2H--H20, (10:15:3:12)), 0.92 (iso-C3HTOH--25% NH4OH, (7:4:6)), 0.56 (iso-C3HTOH --25% NH4OH--H20, C7:1:2)), 0.95 (CsHsN--CH3COCH3--H20, (1:1:2))（TLCon SilufolUV-254 板，用保利试剂显露斑点 [5 ] 和来自它们的紫外线吸收 [3]）。电泳迁移率：1.5（在Whatman No. 1纸上电泳，pH 1.9，450 V，7 mA，沉积标准：人胰岛素B链的双-S-磺酸盐）。UV 吸收，ima x 267-269 nm，log ~，4.04 (1% CH3CO2H)。氨基酸分析：Asp 3.10 (3)、Thr 1.67 (2)、Ser

  DOI：

  10.1007/bf00714941
• 作为产物：
  描述：

  L-脯氨酸 在 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 生成 苄氧羰基-L-脯氨酸 4-硝基苯基酯
  参考文献：
  名称：

  脯氨酸衍生的手性半三明治钌配合物催化的转移加氢反应

  摘要：

  使用由脯氨酸与苯基，乙基或苄基制得的螯合二胺代替配位臂之一上的氢来制备手性钌半三明治复合物。这些复合物中的三种以单一非对映异构体形式获得，其构型通过X射线晶体学鉴定。该络合物是可回收的催化剂，用于在水中将酮还原为手性醇。通过NMR光谱法和同位素标记实验将氢化钌物质鉴定为活性物质。当苯基直接与衍生自脯氨酸的二胺配体上的伯胺连接时，可获得最大的对映选择性。 酮与钌的水溶性半夹心络合物与衍生自脯氨酸的手性配体可在水中进行酮的转移加氢反应，当苯基位于脯氨酸类手性配体上时，对映体选择性更好。

  DOI：

  10.1007/s12039-016-1151-8

文献信息

• Amino acids and peptides. XXIX. Synthesis of peptide fragments related to active center of eglin c and studies on the relationship between their structure and their inhibitory activity against cathepsin G and .ALPHA.-chymotrypsin.
  作者：Kazunori NAKABAYASHI、Satoshi TSUBOI、Taizo FUJIMOTO、Yoshio OKADA、Yoko NAGAMATSU、Junichiro YAMAMOTO

  DOI：10.1248/cpb.38.3249

  日期：——

  H-Ser-Pro-Val-Thr-Leu-Asp-Leu-Arg-Tyr-OMe, corresponding to the sequence 41-49 of eglin c, inhibited human leukocyte cathepsin G and α-chymotrypsin. In order to gain further insight into the relationship between the structure and the inhibitory activity against cathepsin G and α-chymotrypsin, peptide fragments related to the above nonapeptide were synthesized by a conventional solution method and their inhibitory activities were examined. The smallest peptide which exhibited inhibitory effects on the above envymes was H-Pro-Val-Thr-Leu-OMe, corresponding to the sequence 42-45 of eglin c.

  H-Ser-Pro-Val-Thr-Leu-Asp-Leu-Arg-Tyr-OMe，对应于eglin c的第41-49位序列，对人类白细胞组织蛋白酶G和α-胰凝乳蛋白酶具有抑制作用。为了更深入地了解其结构与对组织蛋白酶G和α-胰凝乳蛋白酶抑制活性之间的关系，通过常规液相方法合成了与上述九肽相关的片段，并检测了它们的抑制活性。对上述酶表现出抑制作用的最小肽是H-Pro-Val-Thr-Leu-OMe，对应于eglin c的第42-45位序列。
• Novel esterifying agents, and their production and use
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US03976635A1

  公开（公告）日：1976-08-24

  A process for esterifying organic carboxylic acids which comprises reacting an organic carboxylic acid with a carbonic acid ester of the formula: ##EQU1## wherein R is an organic group and X and Y are each a negative group in the presence of a basic substance to make esterified the carboxyl group in the organic carboxylic acid. The process is advantageous in affording the objective carboxylic ester in a good yield within a short time by a simple operation under a mild reaction condition.

  一种酯化有机羧酸的方法，包括将有机羧酸与碳ic酸酯反应如下公式：其中R是有机基团，X和Y分别是负离子基团，在碱性物质存在下使有机羧酸中的羧基酯化。该工艺的优点在于，在温和的反应条件下，通过简单的操作，可以在短时间内以较高的收率获得所需的羧酸酯。
• Asymmetric synthesis. Metal complex mediated synthesis of chiral glycine by enantioselective proton exchange
  作者：Zdravko. Dokuzovic、Nicholas K. Roberts、Jeffery F. Sawyer、John. Whelan、B. Bosnich

  DOI：10.1021/ja00268a051

  日期：1986.4

  On etudie l'echange selectif des protons methylenes d'un coordinat glycine coordine. On montre aussi que la vitesse de l'echange peut etre employee pour produire de la glycine chirale a n'importe quel degre de purete chirale. Le systeme choisi est [Co((S,S)-proam)(picgly)] + un complexe de Co(III) contenant 2 coordinats tridentes dont l'un contient un reste glycine (proam=iminodimethylene-2,2' bis-pyrrolidine;

  在 etudie l'echange selectif des protons 亚甲基 d'un coordinat 甘氨酸 coordine。On montre aussi que la vitesse de l'echange peut etre employee pour produire de la Glyine chirale a n'importe quel degre de purete chirale。Le systeme choisi est [Co((S,S)-proam)(picgly)] + un complexe de Co(III) contenant 2 coordinats tridentes dont l'un contient un reste gcine (proam=亚氨基二甲基-2,2' bis-吡咯烷；picgly=N-吡啶甲酰基甘氨酸）
• Basicities and Nucleophilicities of Pyrrolidines and Imidazolidinones Used as Organocatalysts
  作者：Feng An、Biplab Maji、Elizabeth Min、Armin R. Ofial、Herbert Mayr

  DOI：10.1021/jacs.9b11877

  日期：2020.1.22

  the attack of the amines at the electrophiles to be determined. The resulting second-order rate constants k2 followed the correlation log k2(20 °C) = sN(N + E), where electrophiles are characterized by one parameter (E) and nucleophiles are characterized by the two solvent-dependent parameters N and sN. In this way, the organocatalysts A1-A32 were integrated in our comprehensive nucleophilicity scale

  有机催化反应中常用的 32 种吡咯烷和咪唑烷酮的 Brønsted 碱度 pKaH（即共轭酸的 pKa）已在乙腈溶液中使用 CH 酸作为指示剂通过光度法测定。大多数研究的吡咯烷的碱性范围为 16 < pKaH < 20，而咪唑烷酮的碱性明显较低 (10 < pKaH < 12)。2-(三氟甲基)吡咯烷 (A14, pKaH 12.6) 和 2-咪唑鎓甲基取代的吡咯烷 A21 (pKaH 11.1) 超出了吡咯烷的典型范围，其碱度与咪唑烷酮的碱度相当。这 32 种有机催化剂与二苯甲基离子 (Ar2CH+) 和结构相关的醌甲基化物（用于量化亲核反应性的常见参考亲电试剂）的反应动力学已通过光度计测量。大多数反应遵循二级动力学，胺一级反应，亲电试剂一级反应。由于胺在亲电子试剂上的初始攻击的可逆性，随后中间体铵离子的速率决定性去质子化，观察到咪唑烷酮和几种携带大量 2-取代基的吡咯烷的反应更复杂的动力学。在
• Synthesis, characterisation and in vitro cytotoxicity studies of a series of chiral platinum(II) complexes based on the 2-aminomethylpyrrolidine ligand: X-ray crystal structure of [PtCl2(R-dimepyrr)] (R-dimepyrr=N-dimethyl-2(R)-aminomethylpyrrolidine)
  作者：Connie I. Diakos、Mei Zhang、Philip J. Beale、Ronald R. Fenton、Trevor W. Hambley

  DOI：10.1016/j.ejmech.2008.12.022

  日期：2009.7

  A series of platinum(II) complexes were synthesised based on the enantiomerically pure amino acid proline. Novel synthetic pathways were developed, adapted from standard peptide chemistry, to produce the 2-aminomethylpyrrolidine (pyrr) ligand and its derivatives with differing arrangements of methyl substituents at the exocyclic amine sites. The crystal structure of [PtCl2(R-dimepyrr)] (R-dimepyrr = N

  基于对映体纯的氨基酸脯氨酸合成了一系列铂（II）配合物。根据标准肽化学，开发了新的合成途径，以产生2-氨基甲基吡咯烷（pyrr）配体及其衍生物，其在环外胺位点具有不同的甲基取代基排列。[PtCl 2（R -dimepyrr）]（R -dimepyrr =  N，N-二甲基-2（R）-氨基甲基吡咯烷），并且五元配体环已显示为包膜构象。对卵巢癌A2780肿瘤细胞系及其顺铂耐药变体A2780cisR进行了细胞毒性研究。尽管胺基团增加了很大的空间体积，但与顺铂相比，几种药物仍具有显着的良好活性，并且某些化合物与顺铂缺乏交叉耐药性。