叔丁氧羰基-S-3-硝基-2-吡啶亚磺酰基-L-半胱氨酸 | 76880-29-0

• 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: 叔丁氧羰基-S-3-硝基-2-吡啶亚磺酰基-L-半胱氨酸
• 英文名称: Boc-Cys(NPys)-OH
• 英文别名: (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[(3-nitropyridin-2-yl)disulfanyl]propanoic acid
• CAS: 76880-29-0
• 化学式: C₁₃H₁₇N₃O₆S₂
• 分子量: 375.426
• InChiKey: OVTLOLNDKQUMRH-QMMMGPOBSA-N

物化性质

• 熔点：
  ~160 °C (dec.)
• 沸点：
  553.9±50.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  在指定条件下稳定，远离氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  185
• 氢给体数：
  2
• 氢受体数：
  9

安全信息

• 安全说明：
  S22,S24/25

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Boc-cys(npys)-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: Boc-cys(npys)-oh
CAS number: 76880-29-0

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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: C13H17N3O6S2
Molecular weight: 375.4

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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, sulfur 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：

  叔丁氧羰基-S-3-硝基-2-吡啶亚磺酰基-L-半胱氨酸 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到(2R)-2-氨基-3-(3-硝基吡啶-2-基)二硫基丙酸
  参考文献：
  名称：

  A novel heterobifunctional linker for facile access to bioconjugates

  摘要：

  本文介绍了一种新型杂多功能连接体分子的简便合成方法。该连接体含有一个具有硫醇反应活性的硝基吡啶二硫醚基团（Npys）和一个具有醛反应活性的氨基氧基团，这两个基团具有形成二硫键和肟键的倾向。在有效制备肽-寡核苷酸共轭物的过程中，已经证明了该连接物分子可交联不同的生物大分子。本文所报道的连接物可以作为一种有用的工具，用于不同的但功能适当的生物大分子的交叉偶联。

  DOI：

  10.1039/b518151h
• 作为产物：
  描述：

  2-氯-3-硝基吡啶 在 吡啶 、 磺酰氯 、 TEA 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 7.0h， 生成 叔丁氧羰基-S-3-硝基-2-吡啶亚磺酰基-L-半胱氨酸
  参考文献：
  名称：

  A New Method for the Preparation of 3-Nitro-2-pyridinesulfenyl Chloride and One-Pot Syntheses ofN(α)-tert-butoxycarbonyl-S-3-nitro-2-pyridinesulfenyl Derivatives of Cysteine and D-Penicillamine

  摘要：

  通过 3-硝基-2-吡啶苄基硫化物与硫酰氯的反应制备了 3-硝基-2-吡啶硫酰氯。使用 4-甲氧基苄基 3-硝基-2-吡啶硫化物完成了半胱氨酸和 D-青霉胺的 N (δ)- 叔丁氧羰基-S-3-硝基-2-吡啶亚磺酰基衍生物的一锅合成。

  DOI：

  10.1055/s-1994-25394

文献信息

• Pyrrolidine derivatives
  申请人：——

  公开号：US20020049243A1

  公开（公告）日：2002-04-25

  The present invention relates to pyrrolidine derivatives and dimeric forms and/or pharmaceutically acceptable esters, and/or salts thereof. The compounds are useful as inhibitors of metalloproteases, e.g. zinc proteases, particularly zinc hydrolases, and which are effective in treating disease states are associated with vasoconstriction of increasing occurrences.

  本发明涉及吡咯烷衍生物及其二聚体形式和/或药用可接受的酯和/或盐。这些化合物可用作金属蛋白酶抑制剂，例如锌蛋白酶，特别是锌水解酶，对治疗与血管收缩增加发生相关的疾病状态有效。
• [EN] DUAL DISULFIDE DRUG CONJUGATES<br/>[FR] CONJUGUÉS DE MÉDICAMENTS À DEUX GROUPES DISULFURE
  申请人：ENDOCYTE INC

  公开号：WO2016168471A1

  公开（公告）日：2016-10-20

  The invention described herein pertains to dual disulfide drug conjugates. In particular, the invention described herein pertains to dual disulfide drug conjugates that target the folate receptor for delivery of conjugated drugs to a mammalian recipient. Also described are methods of making and using dual disulfide drug conjugates.

  本发明涉及双二硫醚药物共轭物。具体而言，本发明涉及双二硫醚药物共轭物，其靶向叶酸受体，用于将共轭药物传递给哺乳动物接受者。还描述了制备和使用双二硫醚药物共轭物的方法。
• [EN] CONJUGATES OF GARFTASE INHIBITORS<br/>[FR] CONJUGUÉS D'INHIBITEURS DE LA GARFTASE
  申请人：ENDOCYTE INC

  公开号：WO2016089879A1

  公开（公告）日：2016-06-09

  The invention described herein pertains to conjugates of GARFTase inhibitors. In particular, the invention described herein pertains to conjugates of GARFTase inhibitors that target the folate receptor for delivery of conjugated drugs to a mammalian recipient. Also described are methods of making and using conjugates of GARFTase inhibitors.

  本发明涉及GARFTase抑制剂的共轭物。具体来说，本发明涉及针对叶酸受体的GARFTase抑制剂的共轭物，用于将共轭药物传递给哺乳动物受体。还描述了制备和使用GARFTase抑制剂共轭物的方法。
• 1-Ethoxyethylidene, a New Group for the Stepwise SPPS of Aminooxyacetic Acid Containing Peptides
  作者：Stéphanie Foillard、Martin Ohsten Rasmussen、Jesus Razkin、Didier Boturyn、Pascal Dumy

  DOI：10.1021/jo701628k

  日期：2008.2.1

  procedures for the preparation of more complex aminooxy-peptides. We have studied the coupling of modified Fmoc-lysine containing either N-Boc- or N,N‘-bis-Boc-protected aminooxyacetic acids (Aoa) during the elongation of the peptide chain and found that none of them is adequate. To circumvent this limitation, we propose to protect the Aoa moiety with a 1-ethoxyethylidene group (Eei) to provide 2-(1-ethoxye

  十多年来，肟醚连接已被证明是制备各种肽结合物的最有效技术之一。然而，尽管有许多报道，但是含氨氧基的肽的制备仍在其掺入过程中或通过肽链延长而受到NH-O功能的N-过度酰化的阻碍。这限制了在最后的酰化步骤引入受保护的NH-O功能，并阻止了使用标准固相肽合成（SPPS）程序来制备更复杂的氨氧基肽。我们已经研究了包含N -Boc-或N，N的修饰Fmoc-赖氨酸的偶联'-双-Boc保护的氨氧基乙酸（Aoa）在肽链的延长过程中，发现没有一个是足够的。为了规避此限制，我们建议使用1-乙氧基亚乙基（Eei）保护Aoa部分，以提供2-（1-乙氧基亚乙基氨基氧基）乙酸构件。我们表明，Eei基团与标准SPPS条件完全兼容，并且可以安全地将氨氧基官能团多次掺入正在生长的肽中。由于Eei保护的Aoa在肽合成中仍保持与正常氨基酸一样的柔韧性，因此可能成为直接制备氨氧基肽的规则。
• Conjugates of Ciprofloxacin and Levofloxacin with Cell-Penetrating Peptide Exhibit Antifungal Activity and Mammalian Cytotoxicity
  作者：Natalia Ptaszyńska、Katarzyna Gucwa、Katarzyna Olkiewicz、Mateusz Heldt、Marcin Serocki、Anna Stupak、Dorota Martynow、Dawid Dębowski、Agata Gitlin-Domagalska、Jan Lica、Anna Łęgowska、Sławomir Milewski、Krzysztof Rolka

  DOI：10.3390/ijms21134696

  日期：——

  Seven conjugates composed of well-known fluoroquinolone antibacterial agents, ciprofloxacin (CIP) or levofloxacin (LVX), and a cell-penetrating peptide transportan 10 (TP10-NH2) were synthesised. The drugs were covalently bound to the peptide via an amide bond, methylenecarbonyl moiety, or a disulfide bridge. Conjugation of fluoroquinolones to TP10-NH2 resulted in congeners demonstrating antifungal in vitro activity against human pathogenic yeasts of the Candida genus (MICs in the 6.25–100 µM range), whereas the components were poorly active. The antibacterial in vitro activity of most of the conjugates was lower than the activity of CIP or LVX, but the antibacterial effect of CIP-S-S-TP10-NH2 was similar to the mother fluoroquinolone. Additionally, for two representative CIP and LVX conjugates, a rapid bactericidal effect was shown. Compared to fluoroquinolones, TP10-NH2 and the majority of its conjugates generated a relatively low level of reactive oxygen species (ROS) in human embryonic kidney cells (HEK293) and human myeloid leukemia cells (HL-60). The conjugates exhibited cytotoxicity against three cell lines, HEK293, HepG2 (human liver cancer cell line), and LLC-PK1 (old male pig kidney cells), with IC50 values in the 10–100 µM range and hemolytic activity. The mammalian toxicity was due to the intrinsic cytoplasmic membrane disruption activity of TP10-NH2 since fluoroquinolones themselves were not cytotoxic. Nevertheless, the selectivity index values of the conjugates, both for the bacteria and human pathogenic yeasts, remained favourable.

  七种由知名的氟喹诺酮类抗菌药物环丙沙星（CIP）或左氧氟沙星（LVX）与细胞穿透肽运输素10（TP10-NH2）组成的共轭物被合成。这些药物通过酰胺键、亚甲基羰基或二硫桥与肽共价结合。将氟喹诺酮类药物与TP10-NH2结合导致所得的同系物在体外显示出对人类致病酵母假丝酵母属（Candida属）的抗真菌活性（最小抑菌浓度在6.25-100 µM范围内），而其组分的活性较差。大多数共轭物的体外抗菌活性低于CIP或LVX的活性，但CIP-S-S-TP10-NH2的抗菌效果与母体氟喹诺酮类相似。此外，对于两种代表性的CIP和LVX共轭物，显示出了快速的杀菌效果。与氟喹诺酮类相比，TP10-NH2及其大多数共轭物在人类胚胎肾细胞（HEK293）和人骨髓白血病细胞（HL-60）中产生的活性氧自由基（ROS）水平相对较低。这些共轭物对三种细胞系（HEK293、HepG2（人肝癌细胞系）和LLC-PK1（老年公猪肾细胞））表现出细胞毒性，IC50值在10-100 µM范围内，并具有溶血活性。哺乳动物毒性是由于TP10-NH2的固有胞质膜破坏活性，因为氟喹诺酮类药物本身并不具有细胞毒性。然而，这些共轭物对细菌和人类致病酵母的选择性指数值仍然有利。