Boc-D-烯丙基甘氨酸 | 170899-08-8

• 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-烯丙基甘氨酸
• 中文别名: N-BOC-D-烯丙基甘氨酸；BOC-D-烯丙基甘氨酸.二环己胺；叔丁氧羰基-D-烯丙基甘氨酸；2-烯丙基-N-BOC-D-甘氨酸二环己胺盐
• 英文名称: N-(tert-butoxycarbonyl)-D-allylglycine
• 英文别名: (R)-2-((tert-butoxycarbonyl)amino)pent-4-enoic acid；(R)-N-Boc-allylglycine；Boc-D-allyl-Gly-OH；Boc-D-allylglycine；(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pent-4-enoic acid
• CAS: 170899-08-8
• 化学式: C₁₀H₁₇NO₄
• 分子量: 215.249
• InChiKey: BUPDPLXLAKNJMI-SSDOTTSWSA-N

物化性质

• 沸点：
  355.52°C (rough estimate)
• 密度：
  1.1835 (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)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  6
• 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

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 海关编码：
  2924199090
• 危险类别：
  IRRITANT
• 储存条件：
  请将密封存储在阴凉干燥的环境中。

SDS

Name:	(R)N-BOC-Allylglycine 95% (98% E.E.) Material Safety Data Sheet
Synonym:	(R)-N-tert-Butoxycarbonyl-2-Amino-4-Pentenoic Acid
CAS:	170899-08-8

Section 1 - Chemical Product MSDS Name:(R)N-BOC-Allylglycine 95% (98% E.E.) Material Safety Data Sheet
Synonym:(R)-N-tert-Butoxycarbonyl-2-Amino-4-Pentenoic Acid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
170899-08-8	(R)N-BOC-Allylglycine	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. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Runoff from fire control or dilution water may cause pollution.
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:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation. 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 cool, dry place. Store in a tightly closed container.

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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# 170899-08-8: 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: Viscous liquid
Color: yellow
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: C10H17NO4
Molecular Weight: 215.25

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not currently available.
Conditions to Avoid:
None reported.
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# 170899-08-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(R)N-BOC-Allylglycine - 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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
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# 170899-08-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 170899-08-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 170899-08-8 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：

  Boc-D-烯丙基甘氨酸 在 氯甲酸乙酯 、 三乙胺 、 ammonium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以90%的产率得到(R)-tert-butyl (1-amino-1-oxopent-4-en-2-yl)carbamate
  参考文献：
  名称：

  肽聚糖前体酰胺化对粪肠球菌和结核分枝杆菌l，d-转肽酶活性的关键影响

  摘要：

  细菌细胞壁肽聚糖含有组装成分支肽的不寻常的l和d氨基酸。由于难以接近底物和进行适当的聚合测定，阻碍了对聚合物生物合成的了解。在这里，我们报告了由两种病原细菌粪肠球菌和结核分枝杆菌的肽聚糖前体的肽茎的完整合成，以及通过l，d进行灵敏的衍生化后化合测定的发展转肽酶。访问系列干的肽表明游离羧基的酰胺化即是最佳酶活性必需的，特别是二氨基庚二酸（DAP）的酰胺化了的交联活性的残基L，d -transpeptidase LDT MT2从结核分枝杆菌。因此，条件突变体的构建确立了AsnB的重要作用，表明该DAP酰胺基转移酶是抗分枝杆菌药物开发的有吸引力的靶标。

  DOI：

  10.1002/chem.201706082
• 作为产物：
  描述：

  在 甲醇 、 sodium tetrahydroborate 、 重铬酸吡啶 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 Boc-D-烯丙基甘氨酸
  参考文献：
  名称：

  Chiral electrophilic “glycinal” equivalents. New synthons for optically active α-amino acids and 4-substituted 2-oxazolidinones

  摘要：

  The thermal reaction of 3-[(IS)-2-alkoxy-1-apocamphanecarbonyl]-2-oxazolones (21a-c) with dialkyl azodicarboxylates (9) results in exclusive formation of [4 + 2] type cycloadducts (22 and 23) with moderate levels of diastereofacial selection (up to 72% d.e.). The diastereomers thus obtained were readily purified and subsequent treatment with acidic methanol followed by removal of the auxiliary with LiBH4/MeOH (1:2) gave optically pure 4-methoxy-5-hydrazino-2-oxazolidinones (26 and 27), which serve as alpha-aminoaldehyde templates useful for the synthesis of a wide variety of optically active alpha-amino acids as well as 4-alkyl and 4-aryl-2-oxazolidinones. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01077-0

文献信息

• Methylene Analogues of Neopetrosiamide as Potential Antimetastatic Agents: Solid-Supported Syntheses Using Diamino Diacids for Pre-Stapling of Peptides with Multiple Disulfides
  作者：Cameron A. Pascoe、Daniel B. Engelhardt、Albert Remus R. Rosana、Marco J. van Belkum、John C. Vederas

  DOI：10.1021/acs.orglett.1c03532

  日期：2021.12.3

  Neopetrosiamide, a 28-residue peptide from Neopetrosia sp., contains three disulfide bonds and hinders mammalian tumor cell invasion. Proper connectivity of disulfide bonds is crucial for activity. Synthetic replacement of single disulfide bridges with methylene bridges gives active analogues. Pre-stapling of one ring enhances the correct formation of the remaining disulfides by reducing isomeric possibilities

  Neopetrosiamide 是一种来自Neopetrosia sp. 的 28 个残基肽，含有三个二硫键，可阻碍哺乳动物肿瘤细胞的侵袭。二硫键的正确连接对于活性至关重要。用亚甲基桥合成取代单个二硫桥得到活性类似物。一个环的预钉合通过减少异构体的可能性并可能启动正确的 3D 折叠来增强剩余二硫化物的正确形成。新石油酰胺在大肠杆菌中的克隆和表达提供了获得天然线性肽的途径。
• Highly Practical Methodology for the Synthesis of <scp>d</scp>- and <scp>l</scp>-α-Amino Acids, <i>N</i>-Protected α-Amino Acids, and <i>N</i>-Methyl-α-amino Acids
  作者：Andrew G. Myers、James L. Gleason、Taeyoung Yoon、Daniel W. Kung

  DOI：10.1021/ja9624073

  日期：1997.1.1

  step the asymmetric alkylation of pseudoephedrine glycinamide (1) or pseudoephedrine sarcosinamide (2). Practical procedures for the synthesis of 1 and 2 from pseudoephedrine and glycine methyl ester or sarcosine methyl ester, respectively, are presented. Optimum protocols for the enolization and subsequent alkylation of 1 and 2 are described. Alkylation reactions of 1 and 2 are found to be quite efficient

  提供了一种非常实用的合成 d-和 l-α-氨基酸、N-保护的 α-氨基酸和 N-甲基-α-氨基酸的方法的完整细节，其中使用伪麻黄碱甘氨酰胺的不对称烷基化作为关键步骤(1) 或伪麻黄碱肌酰胺 (2)。介绍了分别从伪麻黄碱和甘氨酸甲酯或肌氨酸甲酯合成 1 和 2 的实用程序。描述了 1 和 2 的烯醇化和随后的烷基化的最佳方案。发现 1 和 2 的烷基化反应对于范围广泛的卤代烷底物非常有效，并且产物以高非对映选择性形成。通过在水或水-二恶烷混合物中加热，这些烷基化反应的产物可以有效地水解并且几乎没有外消旋化。该协议为制备高对映体纯度的无盐 α-氨基酸提供了一种非常实用的方法。或者，烷基化产物...
• Step-wise and pre-organization induced synthesis of a crossed alkene-bridged nisin Z DE-ring mimic by ring-closing metathesis
  作者：Nourdin Ghalit、Johan Kemmink、Hans W. Hilbers、Cees Versluis、Dirk T. S. Rijkers、Rob M. J. Liskamp

  DOI：10.1039/b618085j

  日期：——

  total synthesis featuring a cross metathesis and a macrolactamization on a solid support followed by a ring-closing metathesis in solution. Via this route the title compound was obtained in an overall yield of 7% (85% on average for 16 reaction steps). In the second approach, the linear precursor peptide was subjected to ring-closing metathesis and the bicyclic peptide with the correct side chain connectivity

  本文描述了两种方法合成乳链菌肽Z DE片段的硫醚环系统的交叉烯烃桥联模拟物。第一种方法包括分步进行的全合成，其特征是在固体支持物上进行交叉复分解和大内酰胺化，然后在溶液中进行闭环复分解。通过该途径，以7％的总产率获得标题化合物（16个反应步骤平均85％）。在第二种方法中，对线性前体肽进行闭环复分解，并以高达95％的产率获得了具有正确侧链连接模式的双环肽。DE环的双环交叉烯烃桥接模拟物的优选形成表明线性前体肽的有利的预组织。
• Novel Cyclic Biphalin Analogues by Ruthenium-Catalyzed Ring Closing Metathesis: <i>in Vivo</i> and <i>in Vitro</i> Biological Profile
  作者：Azzurra Stefanucci、Wei Lei、Stefano Pieretti、Marilisa Pia Dimmito、Grazia Luisi、Ettore Novellino、Michał Nowakowski、Wiktor Koźmiński、Sako Mirzaie、Gokhan Zengin、John M. Streicher、Adriano Mollica

  DOI：10.1021/acsmedchemlett.8b00495

  日期：2019.4.11

  In this work we report the application of the ring-closing metathesis (RCM) to the preparation of two cyclic olefin-bridged analogues of biphalin (Tyr-d-Ala-Gly-Phe-NH-NH ← Phe ← Gly ← d-Ala ← Tyr), using the second generation Grubbs’ catalyst. The resulting cis- and trans-cyclic isomers were identified, fully characterized, and tested in vitro at μ (ΜΟR), δ (DOR), and κ (KOR) opioid receptors and

  在这项工作中，我们报道了闭环复分解法（RCM）在制备双环蛋白（Tyr- d -Ala-Gly-Phe-NH-NH←Phe←Gly← d -Ala ）的两个环烯烃桥联类似物的制备中的应用。←Tyr），使用第二代Grubbs催化剂。在μ（ΜΟR），δ（DOR）和κ（KOR）阿片受体和体内进行鉴定，完全表征和体外测试生成的顺式和反式异构体具有抗伤害感受的作用。两者均显示在MOR上是完全激动剂，在DOR上是潜在的部分拮抗剂，而KOR激动剂的效力较低。他们还共享后侧脑室（ICV）强烈抗伤害感受作用和静脉内（iv）给药，比含有两个侧链之间的二硫键环biphalin类似物更高d -Cys或d -Pen残基，由先前描述的我们的团体。
• Synthesis of optically active α-(allenyl)- and α-substituted-α-(allenyl)glycines
  作者：Takuya Okada、Naoko Oda、Hiroyuki Suzuki、Kazuhiko Sakaguchi、Yasufumi Ohfune

  DOI：10.1016/j.tetlet.2010.05.042

  日期：2010.7

  The synthesis of various types of optically active α-(allenylsilane-containing)glycines via a chirality-transferring ester-enolate Claisen rearrangement of α-acyloxy-α-alkynylsilanes is described. The conversion of the rearranged products into the optically active silicon-free α-(allenyl)- and α-substituted-α-(allenyl)glycines was achieved by the removal of the Me2PhSi- or TMS group from the allene

  描述了通过α-酰氧基-α-炔基硅烷的手性转移酯-烯醇式克莱森重排合成各种类型的旋光性α-（含烯丙基硅烷的）甘氨酸。通过从丙二烯末端除去Me 2 PhSi-或TMS基团，将重排产物转化为旋光的无硅的α-（烯丙基）-和α-取代的-α-（烯基）甘氨酸。