Fmoc-D-3-(4-噻唑基)丙氨酸 | 205528-33-2

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 丙氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: Fmoc-D-3-(4-噻唑基)丙氨酸
• 中文别名: FMOC-3-(4-噻唑)-D-丙氨酸；N-芴甲氧羰基-D-3-(4-噻唑基)丙氨酸；芴甲氧羰基-D-4-噻唑基丙氨酸；9-芴甲氧羰基-D-4-噻唑基丙氨酸；FMOC-D-4-噻唑丙氨酸；Fmoc-D-4-噻唑丙氨酸；Fmoc-D-3-(4-噻唑基)-丙氨酸
• 英文名称: Fmoc-D-3-(4-thiazolyl)Ala-OH
• 英文别名: Fmoc-D-3-(4-thiazoyl)Ala-OH；(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(thiazol-4-yl)propanoic acid；(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(1,3-thiazol-4-yl)propanoic acid
• CAS: 205528-33-2
• 化学式: C₂₁H₁₈N₂O₄S
• mdl: MFCD00672569
• 分子量: 394.451
• InChiKey: LSBAZFASKHLHKB-LJQANCHMSA-N

物化性质

• 熔点：
  180.2 °C
• 沸点：
  647.5±55.0 °C(Predicted)
• 密度：
  1.2468 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储温度应保持在-15°C。

SDS

Name:	(R)-N-FMOC-4-Thiazoylalanine 95% (98% E.E.) Material Safety Data Sheet
Synonym:	N-(9-Fluorenylmethoxycarbonyl)-4-Thiazoyl-D-Alanine
CAS:	205528-33-2

Section 1 - Chemical Product MSDS Name:(R)-N-FMOC-4-Thiazoylalanine 95% (98% E.E.) Material Safety Data Sheet
Synonym:N-(9-Fluorenylmethoxycarbonyl)-4-Thiazoyl-D-Alanine

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
205528-33-2	(R)-N-FMOC-4-Thiazoylalanine	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# 205528-33-2: 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: 180.2 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: C21H18N2O4S
Molecular Weight: 394.44

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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, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 205528-33-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(R)-N-FMOC-4-Thiazoylalanine - 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# 205528-33-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 205528-33-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 205528-33-2 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

反应信息

• 作为反应物：
  描述：

  Fmoc-D-3-(4-噻唑基)丙氨酸 在 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium 、 1-羟基苯并三唑 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 苯甲醚 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 SM253TII
  参考文献：
  名称：

  重塑Hsp90抑制剂：通过使用二聚抑制剂阻止C末端与Hsp90的结合事件

  摘要：

  热激蛋白90（Hsp90）是一种分子伴侣（90 kDa），起二聚体的作用。这种蛋白质有助于负责癌症发展和进程的400多种蛋白质的折叠，组装和稳定化。抑制Hsp90的功能将同时关闭多种癌症驱动的途径，因为致癌客户严重依赖Hsp90，这使得该分子伴侣成为有希望的抗癌靶标。阻止三磷酸腺嘌呤（ATP）与Hsp90 N末端结合的经典抑制剂对细胞具有高毒性，并会触发细胞内的抗药性机制。这种抗性机制包括大量的生存蛋白，即热休克蛋白70（Hsp70），热休克蛋白27（Hsp27）和热休克因子1（HSF-1）。调节Hsp90 C末端的分子可有效诱导癌细胞死亡，而无需激活耐药机制。在本文中，我们描述了一系列二聚化的C末端Hsp90调节剂的设计，合成和生物结合亲和力。我们表明，这些C末端调节剂的二聚体可协同抑制Hsp90相对于单体。

  DOI：

  10.1002/chem.201603464

文献信息

• Compounds for enzyme inhibition
  申请人：Zhou Han-Jie

  公开号：US20070105786A1

  公开（公告）日：2007-05-10

  Peptide-based compounds including heteroatom-containing, three-membered rings efficiently and selectively inhibit specific activities of N-terminal nucleophile (Ntn) hydrolases associated with the proteasome. The peptide-based compounds include an epoxide or aziridine, and functionalization at the N-terminus. Among other therapeutic utilities, the peptide-based compounds are expected to display anti-inflammatory properties and inhibition of cell proliferation. Oral administration of these peptide-based proteasome inhibitors is possible due to their bioavailability profiles

  基于肽的化合物，包括含杂原子的三元环，能够高效且选择性地抑制与蛋白酶体相关的N-末端亲核（Ntn）水解酶的特定活性。这些基于肽的化合物包括环氧化物或氮杂环丙烷，并在N-末端进行官能化。除了其他治疗用途外，预计这些基于肽的化合物将显示抗炎性能和抑制细胞增殖。由于它们的生物利用度特性，这些基于肽的蛋白酶体抑制剂可以通过口服给药进行。
• Chemically Accessible Hsp90 Inhibitor That Does Not Induce a Heat Shock Response
  作者：Yen Chin Koay、Jeanette R. McConnell、Yao Wang、Seong Jong Kim、Laura K. Buckton、Flora Mansour、Shelli R. McAlpine

  DOI：10.1021/ml500114p

  日期：2014.7.10

  Recent cancer therapies have focused on targeting biology networks through a single regulatory protein. Heat shock protein 90 (hsp90) is an ideal oncogenic target as it regulates over 400 client proteins and cochaperones. However, clinical inhibitors of hsp90 have had limited success; the primary reason being that they induce a heat shock response. We describe the synthesis and biological evaluation of a new hsp90 inhibitor, SM253. The previous generation on which SM253 is based (SM145) has poor overall synthetic yields, low solubility, and micromolar cytotoxicity. By comparison SM253 has relatively high overall yields, good aqueous solubility, and is more cytotoxic than its parent compound. Verification that hsp90 is SM253's target was accomplished using pull-down and protein folding assays. SM253 is superior to both SM145 and the clinical candidate 17-AAG as it decreases proteins related to the heat shock response by 2-fold, versus a 2-4-fold increase observed when cells are treated with 17-AAG.
• DEPSIPEPTIDES AND THEIR THERAPEUTIC USE
  申请人：Karus Therapeutics Limited

  公开号：EP2293845A1

  公开（公告）日：2011-03-16
• Compounds for Enzyme Inhibition
  申请人：Zhou Han-Jie

  公开号：US20090203698A1

  公开（公告）日：2009-08-13

  Peptide-based compounds including heteroatom-containing, three-membered rings efficiently and selectively inhibit specific activities of N-terminal nucleophile (Ntn) hydrolases associated with the proteasome. The peptide-based compounds include an epoxide or aziridine, and functionalization at the N-terminus. Among other therapeutic utilities, the peptide-based compounds are expected to display anti-inflammatory properties and inhibition of cell proliferation. Oral administration of these peptide-based proteasome inhibitors is possible due to their bioavailability profiles.
• US7687456B2
  申请人：——

  公开号：US7687456B2

  公开（公告）日：2010-03-30