Boc-L-beta-高丙氨酸 - CAS号 158851-30-0

物化性质

熔点：

99 °C
沸点：

339.5±25.0 °C(Predicted)
密度：

1.101±0.06 g/cm3(Predicted)
溶解度：

溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。
稳定性/保质期：

常温常压下稳定，避免与强氧化剂接触。

计算性质

辛醇/水分配系数(LogP)：

0.9
重原子数：

14
可旋转键数：

5
环数：

0.0
sp3杂化的碳原子比例：

0.777
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
安全说明：

S22,S24/25
WGK Germany：

3
海关编码：

2924199090
危险类别：

IRRITANT
危险性防范说明：

P261,P305+P351+P338
危险性描述：

H315,H319,H335
储存条件：

密封储存，应存放于阴凉、干燥的库房中。

SDS

SDS：27db0ffac8c3e1fa4ff13d78d4a1a007

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
: Boc-β-Homoala-OH
Product name
CAS-No. : 158851-30-0
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
Not a hazardous substance or mixture according to EC-directives 67/548/EEC or 1999/45/EC.
Label elements
Caution - substance not yet tested completely.
Other hazards - none

Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : (S)-3-(Boc-amino)butyric acid
Boc-L-β-homoalanine
Formula : C9H17NO4
Molecular Weight : 203,24 g/mol

Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
Indication of any immediate medical attention and special treatment needed
no data available

Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

Section 7. HANDLING AND STORAGE
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
no data available

Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation
May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Additional Information
RTECS: Not available

Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
no data available

Section 16. OTHER INFORMATION
Further information
Copyright 2012 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

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)-3-boc-氨基丁酸甲酯	(S)-methyl 3-(tert-butyloxycarbonylamino)butyrate	106539-14-4	C₁₀H₁₉NO₄	217.265
——	tert-butyl N-[(1S)-1-methyl-3-oxopropyl]carbamate	118173-26-5	C₉H₁₇NO₃	187.239
——	(S)-tert-butyl (4-hydroxybutan-2-yl)carbamate	106539-36-0	C₉H₁₉NO₃	189.255
——	(2S,3S)-3-tert-butoxycarbonylamino-1,2-butanediol	154079-54-6	C₉H₁₉NO₄	205.254
3-N-boc-(s)-氨基丁腈	(S)-tert-butyl (1-cyanopropan-2-yl)carbamate	172695-22-6	C₉H₁₆N₂O₂	184.238
Boc-L-丙氨醛	Boc-Ala-H	79069-50-4	C₈H₁₅NO₃	173.212
N-Boc-L-丙氨醇	(S)-2-t-butoxycarbonylaminopropan-1-ol	79069-13-9	C₈H₁₇NO₃	175.228

下游产品

中文名称	英文名称	CAS号	化学式	分子量
(s)-3-boc-氨基丁酸甲酯	(S)-methyl 3-(tert-butyloxycarbonylamino)butyrate	106539-14-4	C₁₀H₁₉NO₄	217.265
——	(S)-tert-butyl (4-hydroxybutan-2-yl)carbamate	106539-36-0	C₉H₁₉NO₃	189.255
——	Boc-[(2R,3S)-β^2,3-hAla]-CO2Me	186494-08-6	C₁₁H₂₁NO₄	231.292
——	Boc-[(S,S)-β^2,3-hAla]-CO2Me	113806-44-3	C₁₁H₂₁NO₄	231.292
——	Boc-S-β-HAla-R-HB-OH	233258-43-0	C₁₃H₂₃NO₆	289.329
——	tert-butyl (1S)-1-methyl-4-diazo-3-oxobutylcarbamate	207924-86-5	C₁₀H₁₇N₃O₃	227.263
——	N-carboxy-(S)-3-aminobutyric acid anhydride	288623-01-8	C₅H₇NO₃	129.115

反应信息

作为反应物：

描述：

Boc-L-beta-高丙氨酸在 N-甲基吗啉、 sodium azide 、水作用下，以四氢呋喃、甲苯为溶剂，反应 0.83h，生成 Boc-Ala^u-NHMe

参考文献：

名称：

A Nonpeptidic Reverse-Turn Scaffold Stabilized by Urea-Based Dual Intramolecular Hydrogen Bonding

摘要：

A novel nonpeptidic reverse-turn scaffold containing urea fragments that are connected by a conformationally constrained D-prolyl-cis-1,2-diaminocyclohexane (D-Pro-DACH) linker is reported. The scaffold adopts a well-defined reverse-turn conformation that is stabilized by dual intramolecular hydrogen bonding in both solution and solid states.

DOI：

10.1021/ol201247x
作为产物：

描述：

(s)-3-boc-氨基丁酸甲酯在 sodium hydroxide 、水作用下，以甲醇为溶剂，反应 2.0h，以98.5%的产率得到Boc-L-beta-高丙氨酸

参考文献：

名称：

具有β-氨基酸和α-氨基氧基酸的“新基序”的设计：具有12 / 10-螺旋的杂合肽的合成

摘要：

杂合肽是由C连接的碳-β-氨基酸酯（R -β- Caa）和衍生自S-乳酸的α-氨基氧酸（R -Ama）制备的。对四肽和六肽进行了广泛的NMR（在CDCl 3溶液中），CD和MD研究，从而鉴定出了稳健的12/10混合螺旋。因此，具有R -β-Caa和R -Ama的二肽重复序列提供了一个“新的基序”，以首次在包含R -Ama的低聚物中实现12/10混合的螺旋。要了解侧链对混合螺旋结构的影响，R -β-Caa/ Ama（在Ama中没有取代）和S -β-hAla/ R-研究了Ama低聚物。NMR研究表明这些杂合肽中存在12/10螺旋，并且发现单体的侧链对其稳定性具有深远的影响。这些观察结果暗示了β-氨基酸倾向于混合的12 / 10-螺旋的倾向决定了这些肽的结构行为。氮和氧原子之间的孤对斥力的结构后果导致新的和有趣的结构基序，其像“伪”的行为β 3，β 2在生成十分之十二混合螺旋-肽。

DOI：

10.1021/jo702242q

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文献信息

Design, Synthesis and Biological Evaluation of a Library of Thiocarbazates and Their Activity as Cysteine Protease Inhibitors

作者：Zhuqing Liu、Michael C. Myers、Parag P. Shah、Mary Pat Beavers、Phillip A. Benedetti、Scott L. Diamond、Amos B. Smith,III、Donna M. Huryn

DOI：10.2174/138620710791054303

日期：2010.5.1

Recently, we identified a novel class of potent cathepsin L inhibitors, characterized by a thiocarbazate warhead. Given the potential of these compounds to inhibit other cysteine proteases, we designed and synthesized a library of thiocarbazates containing diversity elements at three positions. Biological characterization of this library for activity against a panel of proteases indicated a significant preference for members of the papain family of cysteine proteases over serine, metallo-, and certain classes of cysteine proteases, such as caspases. Several potent inhibitors of cathepsin L and S were identified. The SAR data were employed in docking studies in an effort to understand the structural elements required for cathepsin S inhibition. This study provides the basis for the design of highly potent and selective inhibitors of the papain family of cysteine proteases.

最近，我们鉴定出一类新型高效组织蛋白酶L抑制剂，其特点是具有硫卡巴脒头部结构。鉴于这些化合物有可能抑制其他半胱氨酸蛋白酶，我们设计并合成了一系列硫卡巴脒类化合物，这些化合物在三个位点上含有多样性元素。该化合物的生物活性鉴定结果显示，它们对木瓜蛋白酶家族的半胱氨酸蛋白酶相较于丝氨酸、金属蛋白酶以及某些类别的半胱氨酸蛋白酶（如胱天蛋白酶）表现出显著的选择性。我们鉴定出了几个高效的组织蛋白酶L和S抑制剂。通过对接研究，我们利用SAR数据来理解实现组织蛋白酶S抑制所需的结构要素。这项研究为设计高度有效且选择性的木瓜蛋白酶家族半胱氨酸蛋白酶抑制剂奠定了基础。
Thermodynamic Scale of β-Amino Acid Residue Propensities for an α-Helix-like Conformation

作者：Brian F. Fisher、Seong Ho Hong、Samuel H. Gellman

DOI：10.1021/jacs.8b05162

日期：2018.8.1

These measurements depend on formation of a parallel coiled-coil tertiary structure when two peptide segments become linked by thioester formation. One peptide segment contains a "guest" site that accommodates diverse β residues and is distal to the coiled-coil interface. We find that helix propensity is influenced by side chain placement within the β residue [β3 (side chain adjacent to nitrogen) slightly

硫醇-硫酯交换系统已被用于测量不同 β-氨基酸残基参与α-螺旋状构象的倾向。当两个肽段通过硫酯形成连接时，这些测量取决于平行卷曲螺旋三级结构的形成。一个肽段包含一个“客体”位点，可容纳不同的 β 残基，位于卷曲螺旋界面的远端。我们发现螺旋倾向受 β 残基内侧链位置的影响 [β3（与氮相邻的侧链）相对于 β2（与羰基相邻的侧链）略微有利]。先前公认的由五元环掺入产生的螺旋稳定性被量化。
[EN] SUBSTITUTED CYCLOHEXYLAMINE COMPOUNDS<br/>[FR] COMPOSÉS DE CYCLOHEXYLAMINE SUBSTITUÉS

申请人：EPIZYME INC

公开号：WO2016040502A1

公开（公告）日：2016-03-17

The present disclosure provides substituted cyclohexylamine compounds having Formula (I): and the pharmaceutically acceptable salts and solvates thereof, wherein R1, R2a, R2b, R3a, R3b, R4, R5, and R7 are defined as set forth in the specification. The present disclosure is also directed to the use of compounds of Formula I to treat a disorder responsive to the blockade of SMYD proteins such as SMYD3 or SMYD2. Compounds of the present disclosure are especially useful for treating cancer.

本公开提供具有以下式（I）的取代环己胺化合物及其药学上可接受的盐和溶剂，其中R1、R2a、R2b、R3a、R3b、R4、R5和R7如规范中所述。本公开还涉及使用式I的化合物治疗对SMYD蛋白的阻断具有响应的疾病，如SMYD3或SMYD2。本公开的化合物特别适用于治疗癌症。
Substituted Cyclohexylamine Compounds

申请人：EPIZYME, INC.

公开号：US20200123142A1

公开（公告）日：2020-04-23

The present disclosure provides substituted cyclohexylamine compounds having Formula (I): and the pharmaceutically acceptable salts and solvates thereof, wherein R 1 , R 2a , R 2b , R 3a , R 3b , R 4 , R 5 , and R 7 are defined as set forth in the specification. The present disclosure is also directed to the use of compounds of Formula I to treat a disorder responsive to the blockade of SMYD proteins such as SMYD3 or SMYD2. Compounds of the present disclosure are especially useful for treating cancer.

本公开提供具有化学式（I）的替代环己胺化合物及其药用可接受的盐和溶剂化合物，其中R1、R2a、R2b、R3a、R3b、R4、R5和R7如规范中所定义。本公开还涉及使用化合物I的方法来治疗对SMYD蛋白如SMYD3或SMYD2阻断产生反应的疾病。本公开的化合物特别适用于治疗癌症。
A Multifaceted Secondary Structure Mimic Based On Piperidine-piperidinones

作者：Dongyue Xin、Lisa M. Perez、Thomas R. Ioerger、Kevin Burgess

DOI：10.1002/anie.201400927

日期：2014.4.1

that with ideal secondary structures and real interface regions in PPIs. Scaffold 1 presents amino acid side‐chains that are quite separated from each other, in orientations that closely resemble ideal sheet or helical structures, similar non‐ideal structures at PPI interfaces, and regions of other PPI interfaces where the mimic conformation does not resemble any secondary structure. 68 different PPIs

极简二级结构模拟物通常被制成类似于蛋白质-蛋白质相互作用 (PPI) 中的一个界面，从而扰乱它。我们最近提出合适的化学型可以直接与界面区域匹配，而无需考虑二级结构。在这里，我们描述了新化学型1的模块化合成，其溶液态构象集合的模拟，以及与理想二级结构和 PPI 中真实界面区域的相关性。脚手架1呈现彼此完全分离的氨基酸侧链，其方向与理想的片状或螺旋结构非常相似，在 PPI 界面具有相似的非理想结构，以及其他 PPI 界面的模拟构象与任何二级结构不相似的区域. 68 种不同的 PPI，其中1 个匹配孔的构象被识别。还提出了一种新方法来确定极简模拟晶体结构与其溶液构象的相关性。因此，dld - 1 faf以比最小能量溶液状态高0.91 kcal mol -1的构象结晶。

Boc-L-beta-高丙氨酸 | 158851-30-0

物质功能分类

分子结构分类

物化性质

计算性质

安全信息

SDS

上下游信息

反应信息

文献信息

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