N-Fmoc-N-甲基-O-叔丁基-L-丝氨酸 | 197632-77-2

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 丝氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: N-Fmoc-N-甲基-O-叔丁基-L-丝氨酸
• 中文别名: N-芴甲氧羰基-N-甲基-O-叔丁基-L-丝氨酸
• 英文名称: Fmoc-N-Me-Ser(tBu)-OH
• 英文别名: (2S)-2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]-3-[(2-methylpropan-2-yl)oxy]propanoic acid
• CAS: 197632-77-2
• 化学式: C₂₃H₂₇NO₅
• 分子量: 397.471
• InChiKey: PQSAXALAXPNFMG-FQEVSTJZSA-N

物化性质

• 熔点：
  213-218℃
• 沸点：
  557.5±50.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• WGK Germany：
  3
• 海关编码：
  2924299090
• 危险类别：
  IRRITANT
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-N-Me-Ser(tBu)-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: Fmoc-N-Me-Ser(tBu)-OH
CAS number: 197632-77-2

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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, refrigerated.
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: C23H27NO5
Molecular weight: 397.5

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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

制备方法与用途

用途

N-Fmoc-N-甲基-O-叔丁基-L-丝氨酸用于生化试剂，作为氨基酸保护单体。

反应信息

• 作为反应物：
  描述：

  methyl (8S,11S,14S)-14-[[(2S)-2-amino-4-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]-methylamino]-11-methyl-3,18-bis[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethoxy]-10,13-dioxo-9,12-diazatricyclo[13.3.1.12,6]icosa-1(18),2,4,6(20),15(19),16-hexaene-8-carboxylate 、 N-Fmoc-N-甲基-O-叔丁基-L-丝氨酸 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 哌啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  [EN] MACROCYCLIC BROAD SPECTRUM ANTIBIOTICS
  [FR] ANTIBIOTIQUES MACROCYCLIQUES À LARGE SPECTRE

  摘要：

  本文提供了抗菌化合物，其中在某些实施例中，这些化合物具有广谱生物活性。在各种实施例中，这些化合物通过抑制细菌类型1信号肽酶（SpsB）发挥作用，这是细菌中的一种必需蛋白质。还提供了使用所述化合物的药物组合物和治疗方法。

  公开号：

  WO2017084630A1
• 作为产物：
  描述：

  甲醇 、 氯甲酸-9-芴基甲酯 、 O-叔丁基-L-丝氨酸 生成 N-Fmoc-N-甲基-O-叔丁基-L-丝氨酸
  参考文献：
  名称：

  Solid phase synthesis of Fmoc N-methyl amino acids: Application of the Fukuyama amine synthesis

  摘要：

  N-Methyl amino acids and their Fmoc derivatives are synthesized in high yield and purity on solid support using the Fukuyama amine synthesis protocol. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01774-7

文献信息

• Peptide Backbone Composition and Protease Susceptibility: Impact of Modification Type, Position, and Tandem Substitution
  作者：Halina M. Werner、Chino C. Cabalteja、W. Seth Horne

  DOI：10.1002/cbic.201500312

  日期：2016.4.15

  Modification station: We report here a systematic comparison of the enzymatic protection imparted by four backbone modifications commonly employed in the design of protease‐stable analogues of peptides and proteins. These results promise to inform ongoing work to develop biostable mimics with increasingly sophisticated structures and functions.

  修饰位点：我们在这里报告了对在肽和蛋白质的蛋白酶稳定类似物的设计中通常采用的四种主链修饰所赋予的酶促保护作用的系统比较。这些结果有望为正在进行的工作提供信息，以开发具有日益复杂的结构和功能的生物稳定模拟物。
• Enhanced Enzymatic Stability and Antitumor Activity of Daunorubicin-GnRH-III Bioconjugates Modified in Position 4
  作者：Marilena Manea、Ulrike Leurs、Erika Orbán、Zsuzsa Baranyai、Peter Öhlschläger、Andreas Marquardt、Ákos Schulcz、Miguel Tejeda、Bence Kapuvári、József Tóvári、Gábor Mező

  DOI：10.1021/bc100547p

  日期：2011.7.20

  Here, we report on the synthesis, enzymatic stability, and antitumor activity of novel bioconjugates containing the chemotherapeutic agent daunorubicin attached through an oxime bond to various gonadotropin-releasing hormone-III (GnRH-III) derivatives. In order to increase the enzymatic stability of the bioconjugates (in particular against chymotrypsin), 4Ser was replaced by N-Me-Ser or Lys(Ac). A

  在这里，我们报道了新型生物共轭物的合成，酶稳定性和抗肿瘤活性，该生物共轭物包含通过肟键与各种促性腺激素释放激素III（GnRH-III）衍生物连接的柔红霉素。为了提高生物缀合物的酶促稳定性（特别是针对胰凝乳蛋白酶），将4 Ser替换为N-Me -Ser或Lys（Ac）。为了研究游离的ε-氨基对生化特性的影响，还制备了其中4 Lys没有被乙酰化的化合物。在体外通过3-（4,5-二甲基噻唑-2-基）-2,5-二苯基四唑溴化物测定法确定了生物缀合物对MCF-7人乳腺癌，HT-29人结肠和LNCaP人前列腺癌细胞的抑制作用。通过液相色谱与质谱联用分析了它们的稳定性/降解（1）在人血清中，（2）在大鼠肝溶酶体匀浆存在下，（3）在消化酶（胰蛋白酶，胰凝乳蛋白酶和胃蛋白酶）存在下。光谱法。结果表明：（1）所有合成的生物缀合物均具有体外抑制细胞的作用，（2）它们在人血清中至少稳定24小时，（3）在溶酶体匀
• Solid-Phase Synthesis of <i>N</i>-Nosyl- and <i>N</i>-Fmoc-<i>N</i>-Methyl-α-amino Acids
  作者：Maria Luisa Di Gioia、Antonella Leggio、Angelo Liguori、Francesca Perri

  DOI：10.1021/jo070075m

  日期：2007.5.1

  convenient and simple solid-phase synthesis of N-nosyl-N-methyl-α-amino acids and N-Fmoc-N-methyl-α-amino acids, important building blocks for the synthesis of conformationally restricted and protease-resistant natural peptides and peptide analogues. The methodology involves the use of 2-chlorotrityl chloride resin to temporarily protect the carboxylic group of α-amino acids and of diazomethane as

  我们在这里报告的方便和简单的固相合成Ñ -nosyl- ñ -甲基- α氨基酸和Ñ -Fmoc- ñ -甲基- α氨基酸，重要构建块用于合成的构象限制，并且蛋白酶抗性天然肽和肽类似物。该方法包括使用2-氯三苯甲基氯树脂暂时保护α-氨基酸的羧基和重氮甲烷的羧基作为甲基化磺酰胺功能的试剂。对于带有带有适当保护的官能化侧链的α-氨基酸，开发的方法也特别有效。
• <i>N</i> ‐Methylated Analogs of hIAPP Fragments 18–22, 23–27, 33–37 Inhibit Aggregation of the Amyloidogenic Core of the Hormone
  作者：Kamil Rozniakowski、Krystian Galecki、Joanna Wietrzyk、Beata Filip‐Psurska、Justyna Fraczyk、Zbigniew J. Kaminski、Beata Kolesinska

  DOI：10.1002/cbdv.202000842

  日期：2021.1

  found to be inhibited in the presence of N‐methylated peptides 1–3 derived from the 18–22 fragment and by the double methylated peptide H−F(N−Me)GA(N−Me)IL−OH (6). Research on the possibility of using N‐methylated analogs of amyloidogenic amylin cores as inhibitors of hormone aggregation is ongoing, with a focus on finding the minimum concentration of N‐methylated peptides capable of inhibiting the aggregation

  胰淀素 (hIAPP) 聚集导致不溶性沉积物的形成，是 II 型糖尿病发展的因素之一。本研究的目的是找到聚集胰淀素片段 18-22、23-27 和 33-37 的 N-甲基化类似物，它们本身不易聚集，并且会抑制激素的淀粉样蛋白核心的聚集. 包含一个或两个 N 甲基化氨基酸残基的片段 18-22 的类似物均未显示任何聚集趋势。只有源自 23-27 hIAPP 热点的肽 H-F(N-Me)GA(N-Me) IL-OH (6) 没有形成纤维结构。尽管结构中存在 N 甲基化氨基酸，但 33-37 胰淀素片段的所有类似物都具有形成聚集体的能力。N-甲基化肽 1-5 显示出对片段 18-22 聚集的抑制特性。来自 (18-22) H-HSSNN-OH 片段的 N-甲基化肽 1-3 和 H-F(N-Me)GA(N-Me) 显着抑制了 23-27 的淀粉样蛋白生成核心的聚集)IL-OH (6) 片段源自 23-27
• PEPTIDE-COMPOUND CYCLIZATION METHOD
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US20150080549A1

  公开（公告）日：2015-03-19

  An object of the present invention is to provide methods of discovering drugs effective for tough targets, which have conventionally been discovered only with difficulty. The present invention relates to novel methods for cyclizing peptide compounds, and novel peptide compounds and libraries comprising the same, to achieve the above object.

  本发明的目的是提供一种发现对于难以处理的靶点有效的药物的方法，这些药物通常很难被发现。本发明涉及新型的环化肽化合物的方法，以及包含这些化合物的新型肽库，以实现上述目的。