Boc-D-炔丙基甘氨酸 | 63039-46-3

• 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 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: Boc-D-炔丙基甘氨酸
• 中文别名: N-叔丁氧羰基-D-炔丙基甘氨酸；BOC-D-炔丙基甘氨酸；BOC-D-炔丙基甘氨酸.二环己胺；叔丁氧羰基-D-炔丙基甘氨酸
• 英文名称: Boc-D-propargylglycine
• 英文别名: (R)-2-((tert-butoxycarbonyl)amino)pent-4-ynoic acid；N-boc-D-propargylglycine；(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pent-4-ynoic acid
• CAS: 63039-46-3
• 化学式: C₁₀H₁₅NO₄
• 分子量: 213.233
• InChiKey: AMKHAJIFPHJYMH-SSDOTTSWSA-N

物化性质

• 沸点：
  353.22°C (rough estimate)
• 密度：
  1.2177 (rough estimate)
• 稳定性/保质期：

  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 海关编码：
  2924199090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Name:	(R)-N-BOC-Propargylglycine 95% (98% E.E.) Material Safety Data Sheet
Synonym:	(R)-N-tert-Butoxycarbonyl-2-amino-4-pentynoic aci
CAS:	63039-46-3

Section 1 - Chemical Product MSDS Name:(R)-N-BOC-Propargylglycine 95% (98% E.E.) Material Safety Data Sheet
Synonym:(R)-N-tert-Butoxycarbonyl-2-amino-4-pentynoic aci

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
63039-46-3	(R)-N-BOC-Propargylglycine	95%	unlisted

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

---

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.

---

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.

---

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.

---

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.

---

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.

---

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# 63039-46-3: 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.

---

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: Not available.
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: C10H15NO4
Molecular Weight: 213.23

---

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

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 63039-46-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(R)-N-BOC-Propargylglycine - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

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

---

Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

---

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# 63039-46-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 63039-46-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 63039-46-3 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  Boc-D-炔丙基甘氨酸 在 N-甲基吗啉 、 copper(ll) sulfate pentahydrate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 sodium ascorbate 、 tris((4-ethoxycarbonylmethyl)-[1,2,3]triazol-1-ylmethyl)amine 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 44.0h， 生成 tert-butyl N2-(tert-butoxycarbonyl)-N6-((R)-2-tert-butoxycarbonylamino-3-(1-(7-hydroxy-2-oxo-2H-chromen-3-yl)-1H-1,2,3-triazol-4-yl)propanoyl)lysinate
  参考文献：
  名称：

  N6-(2-(R)-Propargylglycyl)lysine 作为可点击的吡咯赖氨酸模拟物

  摘要：

  可点击的模仿者！容易获得的二肽D- Pra- ε - Lys使用改良的荧光蛋白测定法鉴定为高效的可点击吡咯赖氨酸模拟物。它被证明以高产率掺入钙调素中，为用含叠氮化物的香豆素标记提供了一种处理方式。

  DOI：

  10.1002/asia.201000205
• 作为产物：
  描述：

  acetyloxy[[(1,1-dimethylethoxy)carbonyl]amino]acetic acid methyl ester 在 phosphate buffer 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 Boc-D-炔丙基甘氨酸
  参考文献：
  名称：

  Zinc mediated addition of active halides to a glycine cation equivalent: Synthesis of N-Boc-L-propargylglycine

  摘要：

  The reaction of allylic, benzylic and propargylic halides with zinc in the presence of the glycine cation equivalent, methyl N-Boc-2-acetoxyglycine, affords Boc protected amino acid derivatives in high yield. Resolution of methyl N-Boc-propargylglycine with alpha-chymotrypsin affords N-Boc-L-propargylglycine in 99% e.e..

  DOI：

  10.1016/s0040-4039(00)73067-x

文献信息

• TETRACYCLIC CDK9 KINASE INHIBITORS
  申请人：AbbVie Inc.

  公开号：US20150218165A1

  公开（公告）日：2015-08-06

  Disclosed are compounds of Formula (Ia), and pharmaceutically acceptable salts thereof, wherein X, Y, R 1 , R 2 , R 3A , R 3B , and R 4 are as described herein. The compounds may be used as agents in the treatment of diseases, including cancer. Also disclosed are pharmaceutical compositions comprising one or more compounds of Formula (Ia).

  公开了公式(Ia)的化合物，以及其中X、Y、R1、R2、R3A、R3B和R4如本文所述的药用可接受盐。这些化合物可用作治疗疾病(包括癌症)的药物。还公开了包含一个或多个公式(Ia)化合物的药物组合物。
• Discovery of VX-509 (Decernotinib): A Potent and Selective Janus Kinase 3 Inhibitor for the Treatment of Autoimmune Diseases
  作者：Luc J. Farmer、Mark W. Ledeboer、Thomas Hoock、Michael J. Arnost、Randy S. Bethiel、Youssef L. Bennani、James J. Black、Christopher L. Brummel、Ananthsrinivas Chakilam、Warren A. Dorsch、Bin Fan、John E. Cochran、Summer Halas、Edmund M. Harrington、James K. Hogan、David Howe、Hui Huang、Dylan H. Jacobs、Leena M. Laitinen、Shengkai Liao、Sudipta Mahajan、Valerie Marone、Gabriel Martinez-Botella、Pamela McCarthy、David Messersmith、Mark Namchuk、Luke Oh、Marina S. Penney、Albert C. Pierce、Scott A. Raybuck、Arthur Rugg、Francesco G. Salituro、Kumkum Saxena、Dean Shannon、Dina Shlyakter、Lora Swenson、Shi-Kai Tian、Christopher Town、Jian Wang、Tiansheng Wang、M. Woods Wannamaker、Raymond J. Winquist、Harmon J. Zuccola

  DOI：10.1021/acs.jmedchem.5b00301

  日期：2015.9.24

  signaling kinase in immune cells, and identified multiple scaffolds showing good inhibitory activity for this kinase. A particular scaffold of interest, the 1H-pyrrolo[2,3-b]pyridine series (7-azaindoles), was selected for further optimization in part on the basis of binding affinity (Ki) as well as on the basis of cellular potency. Optimization of this chemical series led to the identification of VX-509

  尽管存在几种治疗选择，但是仍然需要针对多种自身免疫疾病的更有效，安全和方便的治疗方法。靶向Janus酪氨酸激酶（JAKs）在细胞信号传导反应中起着重要作用，并且可以促进与疾病相关的异常免疫功能，它已成为开发新型自身免疫性疾病疗法的一种新颖且有吸引力的方法。我们针对免疫细胞中的关键信号激酶JAK3筛选了我们的化合物文库，并鉴定了多个支架对该支架表现出良好的抑制活性。选择了特定的目标支架1 H-吡咯并[2,3- b ]吡啶系列（7-氮杂吲哚），部分基于结合亲和力（K i）以及细胞效能的基础上。该化学系列的优化导致鉴定出一种新型，有效和选择性的JAK3抑制剂VX-509（地加罗非尼），与大鼠移植模型（HvG）相比，它在大鼠宿主体内显示出良好的疗效。基于这些发现，看来VX-509为治疗多种自身免疫性疾病提供了潜力。
• Chloroalanyl and propargylglycyl dipeptides. Suicide-substrate-containing antibacterials
  作者：Kam Sing Cheung、Steven A. Wasserman、Edward Dudek、Stephen A. Lerner、Michael Johnston

  DOI：10.1021/jm00366a015

  日期：1983.12

  A set of dipeptides containing the amino acid residues beta-chloroalanine and propargylglycine, which are mechanism-based inactivators of purified microbial enzymes (alanine racemase and cystathionine gamma-synthase, respectively), have been synthesized, and their antibacterial properties in vitro have been evaluated. Dipeptides containing a single beta-chloro-L-alanyl residue (e.g., 3, 5, 9, and 10)

  合成了一组包含氨基酸残基β-氯丙氨酸和炔丙基甘氨酸的二肽，它们是纯化的微生物酶（分别为丙氨酸消旋酶和胱硫醚γ-合酶）的基于机理的失活剂，并已评估了它们的体外抗菌性能。含有单个β-氯-L-丙氨酰基残基（例如3、5、9和10）或单个L-炔丙基糖基残基（例如12和15）的二肽是有效的抗菌剂。通过将这些残基掺入二肽中，β-氯-L-丙氨酸和L-炔丙基甘氨酸的体外抗生素活性可增加多达4000倍。仅包含单个酶灭活氨基酸以及第二个L-丙氨酰基残基（3、5、12和15）的化合物的活性范围有限：仅无乳链球菌，金黄色葡萄球菌和表皮葡萄球菌敏感。然而，含有两个自杀底物残基的肽[例如，β-Cl-LALA-β-Cl-LALA（8）或LppGly-LppGly（18）]是广谱抗菌剂；在被调查的16种物种中，多达12种是敏感物种。含有氨基末端的L-甲硫酰基（9）或L-净戊酰基（10）残基和羧基末端的β-氯-L-丙氨酰基单
• D-ALA-D-ALA-BASED DIPEPTIDES AS TOOLS FOR IMAGING PEPTIDOGLYCAN BIOSYNTHESIS
  申请人：INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION

  公开号：US20160222430A1

  公开（公告）日：2016-08-04

  Disclosed herein are compositions for assessing peptidoglycan biosynthesis in bacteria using modified dipeptides containing a bioorthogonal tag and applying novel post-labeling methods to label the bioorthogonal tag. The resultant, labeled peptidoglycan structures are amenable for identifying bacteria by microscopic visualization.

  本文披露了一种用含有生物正交标记的修饰二肽评估细菌中肽聚糖生物合成的组合物，并应用新颖的后标记方法来标记生物正交标记。标记后的肽聚糖结构适合通过显微镜观察来识别细菌。
• [EN] 5-[5-[2-(3,5-BIS(TRIFLUOROMETHYL)PHENYL)-2-METHYLPROPANOYLMETHYLAMINO]-4-(4-FLUORO-2-METHYLPHENYL)]-2-PYRIDINYL-2-ALKYL-PROLINAMIDE AS NK1 RECEPTOR ANTAGONISTS<br/>[FR] 5- [5- [2- (3, 5-BIS (TRIFLUOROMÉTHYL) PHÉNYL) -2-MÉTHYLPROPANOYLMÉTHYLAMINO] -4- (4-FLUORO-2-MÉTHYLPHÉNYL) ] -2-PYRIDINYL-2-ALKYL-PROLINAMIDE, ANTAGONISTES DU RÉCEPTEUR NK1
  申请人：GLAXO WELLCOME MFG PTE LTD

  公开号：WO2009138393A1

  公开（公告）日：2009-11-19

  The invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof, wherein R is C1-4 alkyl useful in the treatment of diseases and conditions for which antagonism of NK1 receptor is beneficial.

  该发明提供了一种式（I）的化合物或其药用可接受的盐，其中R为C1-4烷基，在治疗需要NK1受体拮抗作用有益的疾病和症状中有用。