N-[(苯基甲氧基)羰基]-D-苯丙氨酸 4-硝基苯基酯 | 2578-85-0

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 苯丙氨酸类衍生物
• 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: N-[(苯基甲氧基)羰基]-D-苯丙氨酸 4-硝基苯基酯
• 中文别名: 苄氧羰基-D-苯丙氨酸-对硝基苯酯；N-[(苯基甲氧基)羰基]-D-苯丙氨酸4-硝基苯基酯
• 英文名称: p-nitrophenyl N-(benzyloxycarbonyl)-D-phenylalaninate
• 英文别名: Nα-benzyloxycarbonyl-D-phenylalanine p-nitrophenyl ester；N-benzyloxycarbonyl-D-phenylalanine p-nitrophenyl ester；D-4-nitrophenyl N-(benzyloxycarbonyl)phenylalanine；Z-D-phenylalanine 4-nitrophenyl ester；Z-D-Phe-ONp；N-benzyloxycarbonyl-(R)-phenylalanine 4-nitrophenyl ester；(4-nitrophenyl) (2R)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 2578-85-0
• 化学式: C₂₃H₂₀N₂O₆
• mdl: MFCD00069875
• 分子量: 420.422
• InChiKey: TVENQUPLPBPLGU-OAQYLSRUSA-N

物化性质

• 熔点：
  119-121 °C(Solv: ethyl acetate (141-78-6); ethyl ether (60-29-7))
• 沸点：
  626.2±55.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2924299090
• 储存条件：
  应存放在室温、密封且干燥的环境中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Z-D-Phe-ONp
Synonyms: Z-D-phenylalanine 4-nitrophenyl ester

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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-Phe-ONp
CAS number: 2578-85-0

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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: C23H20N2O6
Molecular weight: 420.4

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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：

  N-[(苯基甲氧基)羰基]-D-苯丙氨酸 4-硝基苯基酯 在 1,4-二氧六环 、 甲醇 、 phosphate buffer 、 N,N-didodecyl-N^α-<6-(trimethylammonio)hexanoyl>histidinamide 作用下， 生成 4-硝基苯酚阴离子
  参考文献：
  名称：

  Functionalized vesicular assembly. Enantioselective catalysis of ester hydrolysis

  摘要：

  DOI：

  10.1021/ja00393a068
• 作为产物：
  描述：

  N-苄氧羰基-D-苯丙氨酸 生成 N-[(苯基甲氧基)羰基]-D-苯丙氨酸 4-硝基苯基酯
  参考文献：
  名称：

  STOUTAMIRE, DONALD W.;TIEMAN, CHARLES H.

  摘要：

  DOI：

文献信息

• Enantioselective hydrolysis of amino acid esters by apomyoglobin: perfect kinetic resolution of a phenylalanine derivative
  作者：Katsuhiko Tomisaka、Yasuhiro Ishida、Katsuaki Konishi、Takuzo Aida

  DOI：10.1039/b008403o

  日期：——

  Apoprotein of horse-heart myoglobin promoted enantioselective hydrolysis of 4-nitrophenyl esters of amino acids, which allowed nearly perfect kinetic resolution of racemic N-Boc-phenylalanine ester (Boc-Phe-ONp).

  马心肌红蛋白的载脂蛋白促进氨基酸的 4-硝基苯酯的对映选择性水解，这使得外消旋 N-Boc-苯丙氨酸酯 (Boc-Phe-ONp) 的动力学拆分几乎完美。
• Synthesis and structure of prolinal-containing peptides, and their use as specific inhibitors of prolyl endopeptidases.
  作者：MAKOTO NISHIKATA、HIDEYOSHI YOKOSAWA、SHIN-ICHI ISHII

  DOI：10.1248/cpb.34.2931

  日期：——

  Peptide aldehydes are potent inhibitors of serine and cysteine proteases. In the present work, N-benzyloxycarbonyl (Z) dipeptides containing prolinal at the carboxyl terminus were syntheized as inhibitors of prolyl endopeptidases. Since no aldehyde proton was detected by proton nuclear magnetic resonance (1H-NMR) spectrometry, a cyclic structure was proposed for these peptides. Compounds with a Z-L-X-L-prolinal structure were strong inhibitors of prolyl endopeptidases from the ascidian, Halocynthia roretzi, and Flavobacterium meningosepticum. The potency was in the order of Z-L-Val-L-prolinal≃Z-L-Ile-L-prolinal>Z-L-Phe-L-prolinal>Z-L-Ala-L-prolinal with IC50 values of 10-8-10-6 M order for both enzymes. Conversion of the aldehyde into an alcohol or an acid moiety resulted in a considerable decrease in the inhibitory activity. The diastereomers of Z-L-Phe-L-prolinal were much less inhibitory. This result is not compatible with the reported stereospecifity of the Flavobacterium enzyme for its substrated [T. Yoshimoto, R. Walter and D. Tsuru, J. Biol. Chem., 255, 4786 (1980)]. This implies that the open species binds preferentially to the enzyme active site.

  肽醛是丝氨酸和半胱氨酸蛋白酶的强效抑制剂。在本研究工作中，合成了含羧基末端脯氨醛的N-苄氧羰基（Z）二肽，作为脯氨酰内肽酶的抑制剂。由于通过质子核磁共振（1H-NMR）光谱法未检测到醛质子，因此为这些肽提出了一个环状结构。具有Z-L-X-L-脯氨醛结构的化合物是海鞘Halocynthia roretzi和黄杆菌Flavobacterium meningosepticum的脯氨酰内肽酶的强效抑制剂。其效力顺序为Z-L-Val-L-脯氨醛≈Z-L-Ile-L-脯氨醛>Z-L-Phe-L-脯氨醛>Z-L-Ala-L-脯氨醛，IC50值为10-8-10-6 M，对两种酶均有效。将醛转化为醇或酸部分会导致抑制活性显著降低。Z-L-Phe-L-脯氨醛的差向异构体抑制作用较弱。这一结果与黄杆菌酶对其底物的报道立体特异性不一致。这表明开放型物种优先结合到酶活性位点。
• MARKED TEMPERATURE EFFECT ON THE ENANTIOSELECTIVE HYDROLYSIS IN ARTIFICIAL MEMBRANES
  作者：Ryuichi Ueoka、Yoko Matsumoto、Toshiro Nagamatsu、Shoichi Hirohata

  DOI：10.1246/cl.1984.583

  日期：1984.4.5

  was markedly elevated at temperatures somewhat higher than the phase transitions for the hydrolysis of hydrophobic amino acid esters (p-nitrophenyl N-dodecanoyl-D(L)-phenylalaninate) by a hydrophobic dipeptide (tetradecanoyl-L-histidyl-L-leucine) in the artificial membrane (dialkyldimethylammonium bromides) systems.

  对映选择性在略高于疏水性二肽（十四烷酰基-L-组氨酰基-L-亮氨酸）水解疏水性氨基酸酯（对硝基苯基N-十二烷酰基-D（L）-苯丙氨酸酯）的相变温度下显着提高) 在人造膜（二烷基二甲基溴化铵）系统中。
• Cyclodextrin-Mediated Deacylation of Amino Acid Esters with Marked Stereoselectivity.
  作者：Koichi Goto、Kentaro Nakashima、Osamu Tanoue、Satoshi Nukushina、Isao Toudo、Chikara Imamura、Yasuji Ihara、Yoko Matsumoto、Ryuichi Ueoka

  DOI：10.1248/cpb.50.1283

  日期：——

  With respect to the hydrolysis (deacylation) of Z-D(L)-amino acid esters (N-(benzyloxycarbonyl)-D(L)-amino acid p-nitrophenyl esters) mediated by alpha-, beta- and gamma-cyclodextrins (CyDs), a remarkably high enantioselectivity (L/D=9.0) was observed for the deacylation of Ala substrate with gamma-CyD. The kinetic results on the basis of the Michaelis-Menten principle indicate that the enantioselectivity

  关于由α-，β-和γ-环糊精（CyDs）介导的ZD（L）-氨基酸酯（N-（苄氧基羰基）-D（L）-氨基酸对硝基苯酯）的水解（脱酰）作用，观察到Ala底物与γ-CyD脱酰基的对映选择性非常高（L / D = 9.0）。基于Michaelis-Menten原理的动力学结果表明，对映选择性应主要源自γ-CyD-底物（1：1）复合物形成后底物的脱酰基过程。还介绍了对包合物的计算机建模（分子力学）研究。
• Substrate specificity of an actively assembling amyloid catalyst
  作者：Jason L. Heier、Dorian J. Mikolajczak、Christoph Böttcher、Beate Koksch

  DOI：10.1002/bip.23003

  日期：2017.1

  In the presence of Zn2+, the catalytic, amyloid‐forming peptide Ac‐IHIHIQI‐NH2, was found to exhibit enhanced selectivity for hydrophobic p‐nitrophenyl ester substrates while in the process of self‐assembly. As opposed to the substrate p‐nitrophenyl acetate, which was more effectively hydrolyzed with Ac‐IHIHIQI‐NH2 in its fully fibrillar state, the hydrophobic substrate Z‐L‐Phe‐ONp was converted with

  在 Zn2+ 存在下，发现催化性淀粉样蛋白形成肽 Ac-IHIHIQI-NH2 在自组装过程中对疏水性对硝基苯酯底物表现出增强的选择性。与底物对硝基苯乙酸盐相反，后者在完全原纤维状态下被 Ac-IHIHIQI-NH2 更有效地水解，疏水底物 Z-L-Phe-ONp 以大于 11-的二级速率常数转化当催化剂积极组装时，它会增加数倍。在这种条件下，Z-L-Phe-ONp 的水解速度比亲水性更强且更不稳定的 Boc-L-Asn-ONp 酯的水解速度更快。组装时，催化剂对 Z-Phe-ONp 的 L-对映体也表现出更高的选择性。