(S)-N-FMOC-辛基甘氨酸 | 193885-59-5

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 甘氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: (S)-N-FMOC-辛基甘氨酸
• 英文名称: Fmoc-(L-octylGly)-OH
• 英文别名: Fmoc-AD-OH；Fmoc-octyl-Gly-OH；(S)-Fmoc-2-aminodecanoic acid；Fmoc-(S)-2-aminodecanoic acid；(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}decanoic acid；(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)decanoic acid；(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)decanoic acid
• CAS: 193885-59-5
• 化学式: C₂₅H₃₁NO₄
• 分子量: 409.525
• InChiKey: LSMLSLHVRMSYPT-QHCPKHFHSA-N

物化性质

• 熔点：
  142.6 °C
• 沸点：
  529.77°C (rough estimate)
• 密度：
  1.1538 (rough estimate)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存于阴凉干燥处

SDS

Name:	(S)-N-FMOC-Octylglycine 95% (98% E.E.) Material Safety Data Sheet
Synonym:	(S)-N-(9-Fluorenylmethoxycarbonyl)-2-Aminodecanoic Acid
CAS:	193885-59-5

Section 1 - Chemical Product MSDS Name:(S)-N-FMOC-Octylglycine 95% (98% E.E.) Material Safety Data Sheet
Synonym:(S)-N-(9-Fluorenylmethoxycarbonyl)-2-Aminodecanoic Acid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
193885-59-5	(S)-N-FMOC-Octylglycine	95%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 193885-59-5: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white to off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 142.6 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C25H31NO4
Molecular Weight: 409.52

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 193885-59-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(S)-N-FMOC-Octylglycine - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 193885-59-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 193885-59-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 193885-59-5 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  (S)-N-Fmoc-2-(7’-辛烯基)甘氨酸	(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)dec-9-enoic acid	1262886-64-5	C25H29NO4	407.51
  Fmoc-L-烯丙基甘氨酸	2-(9H-fluoren-9-ylmethoxycarbonylamino)-pent-4-enoic acid	146549-21-5	C20H19NO4	337.375
  氯甲酸-9-芴基甲酯	(fluorenylmethoxy)carbonyl chloride	28920-43-6	C15H11ClO2	258.704
  9-芴甲基-N-琥珀酰亚胺基碳酸酯	N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide	82911-69-1	C19H15NO5	337.332

反应信息

• 作为反应物：
  描述：

  (S)-N-FMOC-辛基甘氨酸 在 三乙基硅烷 、 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 4.0h， 生成 (S)-N-(9-fluorenylmethoxycarbonyl)-2-aminodecanal
  参考文献：
  名称：

  具有不同亲脂性的三氨基酸构件的合成。

  摘要：

  为了获得具有不同亲脂性且最多可携带三个正电荷的不同氨基酸，我们开发了许多新的三氨基酸构件。一组结构单元是通过鸟氨酸，二氨基丙酸和二氨基丁酸的侧链通过氨基还原进行氨乙基延伸而实现的。由二氨基丁酸合成具有氨基乙基延伸的具有烃侧链的第二组三氨基酸。通过相应的Fmoc-L-2-氨基脂肪酸分两步合成了还原胺化反应所需的醛。将这些化合物用Boc-L-Dab-OH还原胺化，得到C4-C8烷基支链的三氨基酸。

  DOI：

  10.1371/journal.pone.0124046
• 作为产物：
  描述：

  (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)dec-4-enoic acid 在 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、413.69 kPa 条件下， 以88.5 mg的产率得到(S)-N-FMOC-辛基甘氨酸
  参考文献：
  名称：

  串联钌-亚烷基催化的交叉复分解/氢化：亲脂氨基酸的合成。

  摘要：

  脂质氨基酸的高效合成可以通过Ru-亚烷基催化的长链烯烃与市售的烯丙基甘氨酸的交叉复分解反应实现。然后可以通过使用废复分解催化剂在温和的反应条件下任选地将所得的不饱和类似物氢化。版权所有©2013欧洲多肽协会和John Wiley＆Sons，Ltd.

  DOI：

  10.1002/psc.2522

文献信息

• [EN] MACROCYCLIC PEPTIDES USEFUL AS IMMUNOMODULATORS<br/>[FR] PEPTIDES MACROCYCLIQUES UTILES COMME IMMUNOMOLDULATEURS
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2016077518A1

  公开（公告）日：2016-05-19

  The present disclosure provides compounds which are immunomodulators and thus are useful for the amelioration of various diseases, including cancer and infectious diseases.

  本公开提供了一些免疫调节剂化合物，因此对于改善各种疾病，包括癌症和传染病，具有用处。
• Antiprotozoal Structure–Activity Relationships of Synthetic Leucinostatin Derivatives and Elucidation of their Mode of Action
  作者：Michael Brand、Lei Wang、Stefano Agnello、Silvia Gazzola、Flavio M. Gall、Luka Raguž、Marcel Kaiser、Remo S. Schmidt、Amélie Ritschl、Jennifer Jelk、Andrew Hemphill、Pascal Mäser、Peter Bütikofer、Michael Adams、Rainer Riedl

  DOI：10.1002/anie.202102153

  日期：2021.7.5

  understanding. The antiprotozoal SAR matched SAR in phospholipid liposomes, where membrane integrity, leaking, and dynamics were studied. The mode of action is discussed based on a structure–activity analysis of derivatives in efficacy, ultrastructural studies in T. brucei, and artificial membrane models, mimicking membrane stability and membrane potential. The main site of antiprotozoal action of natural

  Leucinostatin A 是迄今为止描述的最有效的抗原虫化合物之一，但人们对其构效关系 (SAR) 知之甚少。我们使用布氏锥虫作为原生动物模型生物来测试合成修饰的衍生物，得到简化但活性相同的化合物2 (ZHAWOC6025) 和4 (ZHAWOC6027)，随后在分子的所有区域进行修饰，以获得深入的 SAR 了解。抗原虫 SAR 与磷脂脂质体中的 SAR 相匹配，研究了膜的完整性、渗漏和动力学。基于衍生物功效的结构活性分析、 T. brucei的超微结构研究以及模拟膜稳定性和膜电位的人工膜模型，讨论了作用模式。超微结构分析、电子显微镜和线粒体染色表明，天然和合成的亮氨抑素的抗原虫作用的主要位点在于线粒体内膜的不稳定。布氏锥虫的长期亚致死暴露（200 次传代）和 12'000 个突变体的 siRNA 筛选未显示出对合成衍生物产生抗性的迹象。
• Synthesis of Unnatural LipohilicN-(9H-Fluoren-9-ylmethoxy)carbonyl-Substituted ?-Amino Acids and Their Incorporation into Cyclic RGD-Peptides: A structure-activity study
  作者：Marcus Koppitz、Martin Huenges、Rainer Gratias、Horst Kessler、Simon L. Goodman、Alfred Jonczyk

  DOI：10.1002/hlca.19970800423

  日期：1997.6.30

  Xaa = Ahd or Hd-Gly (1 or 2), a βII′/γ-turn-like arrangement with D-Phe in i+1 position of the β-turn is found. Peptides II with D-Xaa = D-Ahd or Hd-Gly (3 or 4) exhibit a βII′/γ-turn conformation with Gly in i+1 position of the β-turn, whereas II with Ahd instead of D-Xaa, i.e., lacking a D-amino acid in position 4 or 5 (5). adopts no defined conformation. However, in assays of receptor specificity

  的α v /β 3整联在人类肿瘤转移和血管生成有关。已经显示了环（-Arg 1 -Gly 2 -Asp 3 -D-Phe 4 -Xaa 5 -）（I）和环（-Arg 1 -Gly 2 -Asp 3 -Phe 4 -D的序列的结构-Xaa 5 -）（II）以高亲和力结合，而后者对该受体具有高选择性。Xaa和D-Xaa残基接受各种氨基酸。在这里，我们报道了在位置5包含亲脂氨基酸Xaa或D-Xaa的环状Arg-Gly-Asp（RGD）肽的合成，活性和构象分析。对于I而言，它们是（2 S）-2-氨基十六烷酸在II，D-Ahd和Hd-Gly中添加了酸（Ahd）和N'-十六烷基甘氨酸（Hd-Gly），并且出于控制目的，并入了Ahd（图1）。对映体纯的α-氨基酸是通过非对映选择性合成和随后使用酰基转移酶I酶法分离异构体而获得的（方案）。根据Stewart的改进程序，从溴乙酸乙酯和十六烷基胺制备Hd-Gly
• Asymmetric synthesis of ( <i>S</i> )‐α‐(octyl)glycine via alkylation of Ni(II) complex of chiral glycine Schiff base
  作者：Bo Fu、Ryosuke Takeda、Yupiao Zou、Hiroyuki Konno、Hiroki Moriwaki、Hidenori Abe、Jianlin Han、Kunisuke Izawa、Vadim A. Soloshonok

  DOI：10.1002/chir.23281

  日期：2020.12

  derived from of glycine Schiff bases with chiral tridentate ligands, has emerge as a leading methodology for preparation of structurally diverse Tailor‐Made Amino Acids, the key structural units in modern medicinal chemistry, and drug design. Here, we report asymmetric synthesis of derivatives of (S)‐α‐(octyl)glycine ((S)‐2‐aminodecanoic acid) and its N‐Fmoc derivative via alkylation of chiral nucleophilic

  在过去十年中，使用源自甘氨酸席夫碱和手性三齿配体的 Ni(II) 配合物已成为制备结构多样的定制氨基酸的主要方法，这是现代药物化学中的关键结构单元，和药物设计。这里，我们报告的（衍生物的不对称合成小号）-α-（辛基）甘氨酸（（小号）-2-氨基癸酸）和它的Ñ经由手性亲核甘氨酸当量与烷基化衍生物-Fmoc Ñ-辛基溴。在优化的条件下，烷基化以优异的收率（98.1%）和非对映选择性（98.8% de）进行。观察到的立体化学结果和方便的反应条件预示着该方法可用于大规模不对称合成 ( S )-2-氨基癸酸及其衍生物。
• Synthesis and antiproliferative activity of C- and N-terminal analogues of culicinin D
  作者：Freda F. Li、Louise A. Stubbing、Iman Kavianinia、Maria R. Abbattista、Paul W.R. Harris、Jeff B. Smaill、Adam V. Patterson、Margaret A. Brimble

  DOI：10.1016/j.bmcl.2020.127331

  日期：2020.8

  Culicinin D (1), a 10 amino acid peptaibol containing several unusual residues, has been shown to exhibit potent anticancer activity. Previous work in our group towards developing a structure-activity relationship (SAR) for this peptaibol has concentrated on replacement of the synthetically challenging AHMOD (3) and AMD (4) residues, resulting in the discovery of analogues with equivalent or better

  Culicinin D（1）是一种含有10个氨基酸的肽醇，其中含有几个不同的残基，已显示出有效的抗癌活性。我们小组先前为开发该肽的构效关系（SAR）的工作主要集中在替代具有合成挑战性的AHMOD（3）和AMD（4）残基，从而发现了具有同等或更好效价且简化的类似物合成。通过研究N末端脂质尾巴和C末端氨基醇的作用，可扩展此肽酶的SAR ，从而揭示了这些部分对乳腺癌和肺癌细胞系中抗增殖活性的关键作用。