N-苄氧羰基-L-脯氨酸 N-羟基琥珀酰亚胺酯 | 3397-33-9

• 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: N-苄氧羰基-L-脯氨酸 N-羟基琥珀酰亚胺酯
• 中文别名: N-苄氧羰基-L-脯氨酸N-羟基琥珀酰亚胺酯
• 英文名称: Z-proline N-hydroxysuccinimide ester
• 英文别名: Z-Pro-OSu；1-O-benzyl 2-O-(2,5-dioxopyrrolidin-1-yl) (2S)-pyrrolidine-1,2-dicarboxylate
• CAS: 3397-33-9
• 化学式: C₁₇H₁₈N₂O₆
• mdl: MFCD00042757
• 分子量: 346.34
• InChiKey: BDNYCEKWUBRCBJ-ZDUSSCGKSA-N

物化性质

• 熔点：
  88-90 °C
• 沸点：
  502.2±60.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.411
• 拓扑面积：
  93.2
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 安全说明：
  S22,S24/25
• 海关编码：
  2925190090
• 危险性防范说明：
  P280
• 危险性描述：
  H302,H317
• 储存条件：
  -15°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Z-Pro-osu
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-Pro-osu
CAS number: 3397-33-9

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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: C17H18N2O6
Molecular weight: 346.3

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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：

  N-苄氧羰基-L-脯氨酸 N-羟基琥珀酰亚胺酯 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 46.17h， 生成 3-amino-5,6,7,7a-tetrahydro-1H-pyrrolizin-1-one
  参考文献：
  名称：

  啶A1 / A2的合成。

  摘要：

  [反应：见正文]将乙酸叔丁酯的烯醇盐添加到氰胺甲酯17中，然后用LHMDS处理，得到乙烯基脲19，收率为27％。从37和氰基乙酸叔丁酯也获得了乙烯基脲19，收率为50％。19用酰氯31d酰化，然后叔丁基酯水解并用9：1 CH2Cl2 / TFA脱羧，甲氧基乙酸酯进行非常温和的碱性水解，得到4啶A1 / A2（3），产率为45％。第一次合成证实了我们对Jannamidines A1 / A2结构的重新分配。

  DOI：

  10.1021/ol0518784
• 作为产物：
  描述：

  N,N'-二琥珀酰亚胺基碳酸酯 、 N-苄氧羰基-L-脯氨酸 在 吡啶 作用下， 以 乙腈 为溶剂， 生成 N-苄氧羰基-L-脯氨酸 N-羟基琥珀酰亚胺酯
  参考文献：
  名称：

  Synthesis of potent water-soluble tissue transglutaminase inhibitors

  摘要：

  Dipeptide-based sulfonium peptidylmethylketones derived from 6-diazo-5-oxo-L-norleucine (DON) have been investigated as potential water-soluble inhibitors of extracellular transglutaminase. The lead compounds were prepared in four steps and exhibited potent activity against tissue transglutaminase. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.006

文献信息

• Activation of carboxylic acids by pyrocarbonates. Application of di-tert-butyl pyrocarbonate as condensing reagent in the synthesis of amides of protected amino acids and peptides
  作者：Vladimir F. Pozdnev

  DOI：10.1016/0040-4039(95)01412-b

  日期：1995.9

  Amides formation from protected amino acids and peptides was achieved in an easy and convenient one-pot procedure using di-tert-butyl pyrocarbonate as activating agent in the presence of pyridine and ammonium hydrogencarbonate. The method gave good yields and did not induce racemization during the amidation of urethane protected amino acids.

  在吡啶和碳酸氢铵存在下，使用焦碳酸二叔丁酯作为活化剂，通过一种简便的一锅法，可以从受保护的氨基酸和肽形成酰胺。该方法在氨基甲酸酯保护的氨基酸的酰胺化过程中获得了良好的收率并且没有引起外消旋作用。
• Ynamide-Mediated Thiopeptide Synthesis
  作者：Jinhua Yang、Changliu Wang、Silin Xu、Junfeng Zhao

  DOI：10.1002/anie.201811586

  日期：2019.1.28

  two‐step strategy for thiopeptide bond formation with readily available monothiocarboxylic acids as thioacyl donors is described. The α‐thioacyloxyenamide intermediates formed from the ynamides and monothiocarboxylic acids can be purified, characterized, and stored. The balance between their activity and stability enables them to act as effective thioacylating reagents to afford thiopeptide bonds under mild

  不足的合成策略不足以将硫酰胺键位点引入肽主链，因此无法探索作为肽和蛋白质化学生物学工具的硫酰胺替代物的全部潜力。描述了一种新颖的由酰胺介导的两步策略，用于以易于获得的单硫代羧酸作为硫代酰基供体的硫肽键形成。由乙酰胺和一硫代羧酸形成的α-硫代酰氧烯酰胺中间体可以进行纯化，表征和储存。它们的活性和稳定性之间的平衡使它们能够充当有效的硫酰化试剂，在温和的反应条件下提供硫肽键。氨基酸官能团，例如OH，CONH 2，并且在巯基肽合成过程中不需要保护吲哚NH基团。这种策略的模块化性质使得在溶液和固相中都可以将硫酰胺键定点结合到肽主链中。
• Syntheses and properties of dipeptides containing .GAMMA.-aminobutyric acid or its analogues at the C-terminal.
  作者：KAZUHARU IENAGA、KUNIHIKO HIGASHIURA、HIROSHI KIMURA

  DOI：10.1248/cpb.35.1249

  日期：——

  Twelve dipeptides (1-12) containing y-aminobutyric acid (GABA : H-γAbu-OH : 37) at the C-terminal were synthesized. Another six dipeptides (13-18) containing GABA analogues such as γ-amino-β-hydroxybutyric acid [GABOB : H-γAbu (2OH) -OH : 38], β-alanine (39) and ε-aminocapric acid (EACA : εAcp : 40) at the C-terminal were also synthesized. Their properties are presented, together with preliminary findings on the immuno-crossreactivity with antiserum against GABA.

  十二种含有γ-氨基丁酸（GABA：H-γAbu-OH：37）在C末端的双肽（1-12）被合成。另外六种含有GABA类似物，如γ-氨基-β-羟基丁酸[GABOB：H-γAbu（2OH）-OH：38]、β-丙氨酸（39）和ε-氨基壬酸（EACA：εAcp：40）在C末端的双肽（13-18）也被合成。它们的性质被呈现，同时还有与针对GABA的抗血清的免疫交叉反应性的初步发现。
• Angiotensin-converting enzyme inhibitors: Synthesis and structure-activity relationships of potent N-benzyloxycarbonyl tripeptide inhibitors.
  作者：Tadahiro SAWAYAMA、Masatoshi TSUKAMOTO、Takashi SASAGAWA、Kazuya NISHIMURA、Ryuichi YAMAMOTO、Takashi DEGUCHI、Kunihiko TAKEYAMA、Kanoo HOSOKI

  DOI：10.1248/cpb.37.2417

  日期：——

  (Z) tripeptide inhibitors of angiotensin-converting enzyme (ACE) was synthesized. The effect of varying the antepenultimate amino acid residue in this series on the biological activity was studied. Introduction of Lys and Orn residues at the P1 position provided the most potent inhibitors, 25a and 25b (IC50: 3.5 and 4.9 x 10(-9) M, respectively), which exhibited an oral antihypertensive activity. This

  合成了一系列新的含γ-D-Glu的血管紧张素转化酶（ACE）的N-苄氧基羰基（Z）三肽抑制剂。研究了改变该系列中前倒数第二个氨基酸残基对生物活性的影响。在P1位置引入Lys和Orn残基可提供最有效的抑制剂25a和25b（IC50：分别为3.5和4.9 x 10（-9）M），具有口服降压活性。该结果表明，在该系列中，P1位的碱性氨基酸残基在与ACE的S1亚位点的结合中起重要作用。评价了所选化合物的口服降压活性。
• C2 symmetrical nickel complexes derived from α-amino amides as efficient catalysts for the enantioselective addition of dialkylzinc reagents to aldehydes
  作者：Jorge Escorihuela、Belen Altava、M. Isabel Burguete、Santiago V. Luis

  DOI：10.1016/j.tet.2012.11.025

  日期：2013.1

  amides were studied for the enantioselective addition of dialkylzinc reagents to aldehydes. Different structural elements on the ligands seem to play an important role in determining the observed enantioselectivity. Through optimization of structure and reaction conditions, the best ligand provided secondary alcohols in excellent yields (up to 98%) and enantioselectivity of up to 99% ee for (R)-enantiomer

  研究了由α-氨基酰胺衍生的一系列C 2对称的1：2 Ni：L络合物，用于将二烷基锌试剂对映异构地加成到醛中。配体上的不同结构元素似乎在确定观察到的对映选择性中起重要作用。通过的结构和反应条件的优化，最佳配位体以优良产率（高达98％）和高达99％ee的对（对映选择性的提供仲醇ř）-对映体。已经提出了一种过渡状态模型，用于基于DFT级别的计算结果解释所观察到的对映选择性。非常有趣的是，计算表明通过羰基氧的孤对与氨基氢原子的缔合，醛与金属络合物的配位模型。