BOC-(2S,4S)-4-氨基-1-FMOC-吡咯烷-2-羧酸 | 221352-74-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: BOC-(2S,4S)-4-氨基-1-FMOC-吡咯烷-2-羧酸
• 中文别名: (2S,4S)-4-[[叔丁氧羰基]氨基]-1,2-吡咯烷二甲酸1-(9H-芴-9-基甲基)酯
• 英文名称: 4-N-tert-butyloxycarbonylamino-N-9-fluorenylmethyloxycarbonyl-L-cis-proline
• 英文别名: (2S,4S)-N^α-Fmoc-4-N-Boc-aminoproline；(2S,4S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-(tert-butoxycarbonylamino)pyrrolidine2-carboxylic acid；Fmoc-Pro(4-NHBoc)-OH；Fmoc-L-Pro(cis-4-NHBoc)；Boc-(2S,4S)-4-amino-1-Fmoc-pyrrolidine-2-carboxylic acid；cis-4-BocNH-N^α-Fmoc-Pro-OH；N-Boc-cis-4-amino-N-Fmoc-L-proline；Fmoc-(2S,4S)-(4-NHBoc)Pro-OH；(2S,4S)-1-(9H-fluoren-9-ylmethoxycarbonyl)-4-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidine-2-carboxylic acid
• CAS: 221352-74-5
• 化学式: C₂₅H₂₈N₂O₆
• 分子量: 452.507
• InChiKey: FJEXPICLVWOJSE-BTYIYWSLSA-N

物化性质

• 熔点：
  87-89℃
• 沸点：
  650.5±55.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P280
• 危险性描述：
  H302,H317

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (2S, 4S)-Boc-4-amino-1-fmoc-pyrrolidine-2-carboxylic acid
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: (2S, 4S)-Boc-4-amino-1-fmoc-pyrrolidine-2-carboxylic acid
CAS number: 221352-74-5

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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: C25H28N2O6
Molecular weight: 452.5

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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：

  BOC-(2S,4S)-4-氨基-1-FMOC-吡咯烷-2-羧酸 在 二乙胺 、 三氟乙酸 作用下， 以 乙腈 、 二氯甲烷 为溶剂， 反应 1.0h， 以73%的产率得到(4S)-4-氨基-L-脯氨酸
  参考文献：
  名称：

  [EN] TETRAHYDROTHIOPHENE-BASED GABA AMINOTRANSFERASE INACTIVATORS
  [FR] INACTIVATEURS DE LA GABA AMINOTRANSFÉRASE À BASE DE TÉTRAHYDROTHIOPHÈNE

  摘要：

  硫代四氢噻吩及其相关杂环类似物以及相关的GABA氨基转移酶失活方法。

  公开号：

  WO2016145082A1
• 作为产物：
  描述：

  N-(叔丁氧羰基)-4-羟基脯氨酸苄酯 在 吡啶 、 sodium azide 、 palladium on activated charcoal 、 氢气 、 碳酸氢钠 、 三乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 65.0 ℃ 、810.65 kPa 条件下， 反应 74.0h， 生成 BOC-(2S,4S)-4-氨基-1-FMOC-吡咯烷-2-羧酸
  参考文献：
  名称：

  新型 µ 阿片拮抗剂源自 µ 阿片激动剂内吗啡肽和 [Dmt1 ] DALDA (H-Dmt-D-Arg-Phe-Lys-NH2)。

  摘要：

  µ 阿片类激动剂内吗啡肽和 [Dmt 1 ]DALDA（H-Dmt-D-Arg-Phe-Lys-NH 2，Dmt = 2',6'-二甲基酪氨酸）的杂合类似物，含有顺式-4-氨基-Pro，反式合成了肽序列第 2 位的-4-氨基-Pro、顺式-4-氨基乙基-Pro 或顺式-4-胍基乙基-Pro 。没有一种化合物保持高μ阿片类激动剂活性，出人意料的是，顺式-4-氨基-Pro的取代产生了一类新型的强效μ阿片拮抗剂。特别是，化合物 H-Dmt- cis -4-amino-Pro-Trp-Lys-NH 2 (CZ-1) 是一种高度选择性的 µ 阿片拮抗剂，具有 ~1 nM µ 受体结合亲和力。

  DOI：

  10.1111/cbdd.13743

文献信息

• [EN] CYCLIC PEPTIDES AS C5 A RECEPTOR ANTAGONISTS<br/>[FR] PEPTIDES CYCLIQUES EN TANT QU'ANTAGONISTES DU RÉCEPTEUR C5
  申请人：PFIZER

  公开号：WO2018020358A1

  公开（公告）日：2018-02-01

  The invention relates to cyclic peptide derivatives, to their use in medicine, to compositions containing them, to processes for their preparation and to intermediates used in such processes. More particularly the invention relates to cyclic peptide C5a receptor antagonists of formula (Ia)or formula (Ib), or pharmaceutically acceptable salts thereof,wherein R1a, R1b, R2, R3 and R4 areas defined in the description. C5a receptor antagonists are potentially useful in the treatment of a wide range of 1 disorders,including inflammatory disorders and immune disorders.

  这项发明涉及环肽衍生物，它们在医学中的应用，含有它们的组合物，其制备方法以及用于这些方法的中间体。更具体地，该发明涉及公式(Ia)或公式(Ib)的环肽C5a受体拮抗剂，或其药用盐，其中R1a、R1b、R2、R3和R4在描述中有定义。C5a受体拮抗剂潜在地在治疗广泛的疾病中有用，包括炎症性疾病和免疫性疾病。
• Diprolyl nitriles as potent dipeptidyl peptidase IV inhibitors
  作者：Guohua Zhao、Prakash C. Taunk、David R. Magnin、Ligaya M. Simpkins、Jeffrey A. Robl、Aiying Wang、James G. Robertson、Jovita Marcinkeviciene、Doree F. Sitkoff、Rex A. Parker、Mark S. Kirby、Lawrence G. Hamann

  DOI：10.1016/j.bmcl.2005.06.043

  日期：2005.9

  Dipeptidyl peptidase IV (DPP4) is a multifunctional type II transmembrane serine peptidase which regulates various physiological processes, most notably plasma glucose homeostasis by cleaving peptide hormones glucagon-like peptide-1 and glucose-dependent insulinotropic polypeptide. Inhibition of DPP4 is a potentially valuable therapy for type 2 diabetes. Synthesis and structure-activity relationships

  二肽基肽酶IV（DPP4）是一种多功能的II型跨膜丝氨酸肽酶，可通过切割肽激素胰高血糖素样肽1和葡萄糖依赖性促胰岛素多肽来调节各种生理过程，最主要的是血浆葡萄糖稳态。抑制DPP4是治疗2型糖尿病的潜在有价值的疗法。描述了一系列取代的二吡咯基腈的合成与构效关系，从而鉴定了具有测得的DPP4 K（i）为3.6 nM的化合物1。
• Two prolines with a difference: contrasting stereoelectronic effects of 4R/S-aminoproline on triplex stability in collagen peptides [Pro(X)-Pro(Y)-Gly]nElectronic supplementary information (ESI) available: 1H NMR spectra and coupling constant analysis of 3 and 4; synthetic schemes for 3, 4, 5 and 6; FABMS of 3 and 4; MALDI-TOF MS of 5 and 6; HPLC of peptides 5 and 6. See http://www.rsc.org/suppdata/cc/b3/b308581c/
  作者：M. Umashankara、I. Ramesh Babu、Krishna N. Ganesh

  DOI：10.1039/b308581c

  日期：——

  4R/S-Aminoprolines when present in the X-position of collagen peptide [pro(X)-pro(Y)-Gly]n exhibit pH- and stereochemistry-dependent effects on triplex stability.

  在胶原肽[pro(X)-pro(Y)-Gly]n中，当4R/S-氨基脯氨酸位于X位置时，对三重螺旋稳定性表现出pH和立体化学依赖性效应。
• Identification of Novel Low Molecular Weight CXCR4 Antagonists by Structural Tuning of Cyclic Tetrapeptide Scaffolds
  作者：Hirokazu Tamamura、Takanobu Araki、Satoshi Ueda、Zixuan Wang、Shinya Oishi、Ai Esaka、John O. Trent、Hideki Nakashima、Naoki Yamamoto、Stephen C. Peiper、Akira Otaka、Nobutaka Fujii

  DOI：10.1021/jm050009h

  日期：2005.5.1

  found by using two orthogonal cyclic pentapeptide libraries involving conformation-based and sequence-based libraries based on the pharmacophore of a 14-mer peptidic antagonist, 1. Herein, cyclic tetrapeptides derived from replacements of the dipeptide unit (Nal-Gly) with a gamma-amino acid and pseudopeptides cyclized by disulfide and olefin bridges were synthesized to find novel scaffold structures different

  先前通过使用两个正交环状五肽文库发现了一种高效CXCR4拮抗剂化合物2，所述正交五环文库涉及基于14-mer肽拮抗剂1的药效基团的基于构象和基于序列的文库。合成了具有γ-氨基酸的二肽单元（Nal-Gly）以及由二硫键和烯烃桥环合的假肽，以发现不同于环状五肽的新型支架结构。与化合物2相比，这些化合物包含的肽键数量减少。此外，还制备了几种具有Arg（4）侧链化学修饰的类似物（2）。由此，鉴定了具有高至中等CXCR4拮抗活性的几种新的铅。
• Identification of Compounds Modifying A Cellular Response
  申请人：Thastrup Ole

  公开号：US20090239755A1

  公开（公告）日：2009-09-24

  The present invention relates to methods for identifying compounds capable of modulating a cellular response. The methods involve attaching living cells to solid supports comprising a library of test compounds. The test compounds are linked to the solid support via cleavable linkers and may thus be released from the solid supports. Solid supports comprising cells, wherein the cellular response of interest has been modulated are selected and the test compound of the solid support can then be identified. The cellular response may for example be changes in complex formation between proteins.

  本发明涉及识别能够调节细胞反应的化合物的方法。该方法涉及将活细胞附着在包含测试化合物库的固体支撑体上。测试化合物通过可切割的连接剂与固体支撑体连接，因此可以从固体支撑体释放出来。选择细胞被固体支撑体调节了感兴趣的细胞反应的固体支撑体，并且可以鉴定固体支撑体上的测试化合物。细胞反应可以是蛋白质复合物形成的变化，例如。