N-叔丁氧羰基-D-别异亮氨酸 | 55780-90-0

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 异亮氨酸类衍生物
• 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: N-叔丁氧羰基-D-别异亮氨酸
• 中文别名: Boc-D-造血岛羟基；Boc-D-别异亮氨酸；BOC-D-别异亮氨酸
• 英文名称: N-tert-butoxycarbonyl-D-alloisoleucine
• 英文别名: Boc-D-allo-Ile-OH；Boc-D-allo-isoleucine；(2R,3S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid
• CAS: 55780-90-0
• 化学式: C₁₁H₂₁NO₄
• 分子量: 231.292
• InChiKey: QJCNLJWUIOIMMF-JGVFFNPUSA-N

物化性质

• 熔点：
  66-67 °C
• 沸点：
  356.0±25.0 °C(Predicted)
• 密度：
  1.061±0.06 g/cm3(Predicted)
• 稳定性/保质期：

  如果按照规格使用和储存，则不会分解，未有已知危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  请将贮藏器密封保存，并存放在阴凉、干燥处。确保工作环境有良好的通风或排气设施。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Boc-D-allo-Ile-OH
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: Boc-D-allo-Ile-OH
CAS number: 55780-90-0

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C11H21NO4
Molecular weight: 231.3

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  N-叔丁氧羰基-D-别异亮氨酸 在 吡啶 、 chromium(VI) oxide 、 sodium hydroxide 、 diborane 、 乙酰氯 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 7.25h， 生成 N,O-diacetyl-(3S,4R,5S)-isostatine methyl ester
  参考文献：
  名称：

  Synthesis and properties of the eight isostatine stereoisomers

  摘要：

  The eight possible stereoisomers of isostatine, (3S,4R,5S)-4-amino-3-hydroxy-5-methylheptanoic acid, have been synthesized from the four isomeric D- and L-isoleucinals and D- and L-allo-isoleucinals and ethyl lithioacetate. The eight isomers have been compared for the GC retention times of their bis(trifluoroacetyl) methyl ester derivatives and the H-1 NMR properties of the gamma-lactams derived from them. The natural isomer was shown to be the 3S,4R,5S isomer.

  DOI：

  10.1021/jo00037a012
• 作为产物：
  描述：

  (S)-2-甲基丁醛 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 sodium azide 、 硫酸 、 氢气 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 吡啶 、 甲醇 、 乙二醇二甲醚 、 乙醚 、 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， -10.0~50.0 ℃ 、101.33 kPa 条件下， 反应 160.0h， 生成 N-叔丁氧羰基-D-别异亮氨酸
  参考文献：
  名称：

  Lloyd-Williams, Paul; Monerris, Patricia; Gonzalez, Isabel, Journal of the Chemical Society. Perkin transactions I, 1994, # 14, p. 1969 - 1974

  摘要：

  DOI：

文献信息

• Target Identification of Yaku’amide B and Its Two Distinct Activities against Mitochondrial F_oF₁-ATP Synthase
  作者：Kai Kitamura、Hiroaki Itoh、Kaori Sakurai、Shingo Dan、Masayuki Inoue

  DOI：10.1021/jacs.8b07339

  日期：2018.9.26

  four β,β-dialkylated α,β-unsaturated amino acid residues. Growth-inhibitory profile of 1b against a panel of 39 human cancer cell lines is distinct from those of clinically used anticancer drugs, suggesting a novel mechanism of action. We achieved total syntheses of chemical probes based on 1b and elucidated the cellular target and mode of action of 1b. Fluorescent (3, 4) and biotinylated (5, 6) derivatives

  Yaku'amide B (1b) 是一种结构独特的十四肽，带有四个 β,β-二烷基化 α,β-不饱和氨基酸残基。1b 对一组 39 种人类癌细胞系的生长抑制特征与临床使用的抗癌药物不同，表明了一种新的作用机制。我们实现了基于 1b 的化学探针的全合成，并阐明了 1b 的细胞靶点和作用方式。分别制备了 1b 的荧光 (3, 4) 和生物素化 (5, 6) 衍生物用于细胞成像研究和下拉分析。此外，合成了1b的非天然对映体（ent-1b）及其荧光探针（ent-3）用于对照实验。使用 3 和 4 进行的亚细胞定位分析表明，1b 选择性地积聚在 MCF-7 人乳腺癌细胞的线粒体中。6 的下拉分析显示 FoF1-ATP 合酶是 1b 的主要靶蛋白。与这些发现一致，生化活性测定表明 1b 抑制由线粒体 FoF1-ATP 合酶催化的 ATP 产生。值得注意的是，还发现 1b 能够增强 FoF1-ATP 合酶的
• Total synthesis of spiruchostatin B aided by an automated synthesizer
  作者：Shinichiro Fuse、Kumiko Okada、Yusuke Iijima、Asami Munakata、Kazuhiro Machida、Takashi Takahashi、Motoki Takagi、Kazuo Shin-ya、Takayuki Doi

  DOI：10.1039/c0ob01169j

  日期：——

  The total synthesis of a natural productHDAC inhibitor, spiruchostatin B, was successfully achieved. A 5-step synthesis that included an asymmetric aldol reaction was carried out in an automated synthesizer to provide an (E)-(S)-3-hydroxy-7-thio-4-heptenoic acid segment that is the crucial structure of cysteine-containing, depsipeptidic natural products such as spiruchostatins, FK228, FR901375, and largazole for their inhibitory activity against HDACs.

  天然产物HDAC抑制剂spirochostatin B的全合成成功实现。通过自动化合成器执行了一种包含不对称羟醛反应的5步合成路线，得到了(E)-(S)-3-羟基-7-硫-4-庚烯酸片段，这一片段是包含半胱氨酸的脱硫肽类天然产物，如spirochostatins、FK228、FR901375和largazole，它们对HDACs具有抑制活性的关键结构。
• Total synthesis and conformational studies of ceratospongamide, a bioactive cyclic heptapeptide from marine origin
  作者：Fumiaki Yokokawa、Hirofumi Sameshima、Yasuko In、Katsuhiko Minoura、Toshimasa Ishida、Takayuki Shioiri

  DOI：10.1016/s0040-4020(02)00906-7

  日期：2002.9

  The first total synthesis of cis,cis-ceratospongamide (cyclo[l-Pro-l-Ile-Me-oxazoline-l-Phe-l-Pro-thiazole-l-Phe-]) was accomplished and confirmed by X-ray crystal analysis. The heating of cis,cis-ceratospongamide in DMSO converted it not to the trans,trans isomer but to the trans,trans-[d-allo-Ile]-ceratospongamide, which was confirmed by total synthesis. Its solution conformation was constructed

  X射线晶体证实了顺式，顺式-ceratospongamide（环[1-Pro-Ile-Me-恶唑啉-1-Phe-1-Pro-噻唑-1-Phe-]）的第一个全合成反应。分析。DMSO中顺式，顺式-ceratospongamide的加热将其转化为反式，反式异构体，而不是反式，反式-[d-allo-Ile] -ceratospongamide，这已通过全合成得到证实。它的溶液构象是利用ROE交叉峰通过动态模拟退火方法构建的，显示出一个圆扁的环结构，与顺式，顺式的细长结构紧密形成对比。异构体。结果表明，反式，反式-[d-allo-Ile]异构体是顺式，顺式-ceratospongamide的主要热产物。
• One-Pot Enantiomeric Synthesis of Thiazole-Containing Amino Acids: Total Synthesis of Venturamides A and B
  作者：Yi Liu、Peng He、Yang Zhang、Xiangyu Zhang、Jun Liu、Yuguo Du

  DOI：10.1021/acs.joc.8b00244

  日期：2018.4.6

  thiazole-containing amino acid (TCAA) has been established via a cascade disulfide cleavage/thiocarbonylation/intramolecular Staudinger reduction/aza-Wittig/oxidation reaction. Starting from the commercially available amino acid building blocks, a number of TCAAs were prepared in good yields and with excellent optical purities. This method bears features of mild reaction conditions, wide substrate adaptability

  通过级联二硫键裂解/硫代羰基化/分子内斯托丁格还原/氮杂-维蒂希/氧化反应，已经建立了一种有效的一锅法，用于对映体合成含噻唑的氨基酸（TCAA）。从可商购的氨基酸构件开始，以高收率和优异的光学纯度制备了许多TCAA。该方法具有反应条件温和，底物适应性广，官能团耐受性好的特点。环状六肽Venturamides A和B的简明全合成也证明了该方法的强大功能。
• Discovery of the Soluble Guanylate Cyclase Activator Runcaciguat (BAY 1101042)
  作者：Michael G. Hahn、Thomas Lampe、Sherif El Sheikh、Nils Griebenow、Elisabeth Woltering、Karl-Heinz Schlemmer、Lisa Dietz、Michael Gerisch、Frank Wunder、Eva-Maria Becker-Pelster、Thomas Mondritzki、Hanna Tinel、Andreas Knorr、Armin Kern、Dieter Lang、Joerg Hueser、Tibor Schomber、Agnes Benardeau、Frank Eitner、Hubert Truebel、Joachim Mittendorf、Vijay Kumar、Focco van den Akker、Martina Schaefer、Volker Geiss、Peter Sandner、Johannes-Peter Stasch

  DOI：10.1021/acs.jmedchem.0c02154

  日期：2021.5.13

  Herein we describe the discovery, mode of action, and preclinical characterization of the soluble guanylate cyclase (sGC) activator runcaciguat. The sGC enzyme, via the formation of cyclic guanosine monophoshphate, is a key regulator of body and tissue homeostasis. sGC activators with their unique mode of action are activating the oxidized and heme-free and therefore NO-unresponsive form of sGC, which

  在这里，我们描述了可溶性鸟苷酸环化酶（sGC）激活剂runcaciguat的发现，作用方式和临床前表征。sGC酶通过形成环状鸟苷一磷酸而成为机体和组织体内稳态的关键调节剂。sGC活化剂以其独特的作用方式正在活化sGC的氧化且不含血红素，因此没有NO反应形式，它是在氧化应激下形成的。sinaciguat或ataciguat之类的第一代sGC激活剂显示出局限性并已停产。我们克服了第一代sGC激活剂的局限性，并通过高通量筛选鉴定了新的化学类别。通过研究结构与活性之间的关系，可以提高效力和多重溶解度，通透性，新陈代谢以及药物与药物的相互作用参数。45，BAY 1101042）。目前，在临床2期研究中对Runcaciguat进行了研究，以治疗患有慢性肾脏疾病和非增生性糖尿病性视网膜病的患者。