N-叔丁氧羰基-N-甲基-L-苏氨酸 | 101759-72-2

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 苏氨酸类衍生物
• 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-N-甲基-L-苏氨酸
• 英文名称: Boc-MeThr-OH
• 英文别名: Boc-Thr(N-Me)-OH；Boc-L-Thr(OH)-COOH；Boc-N-methyl-L-threonine；(2S,3R)-3-hydroxy-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]butanoic acid
• CAS: 101759-72-2
• 化学式: C₁₀H₁₉NO₅
• 分子量: 233.265
• InChiKey: NHXZARPGSOCYMJ-RQJHMYQMSA-N

物化性质

• 沸点：
  360℃
• 密度：
  1.182
• 闪点：
  171℃

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Boc-N-Me-Thr-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-N-Me-Thr-OH
CAS number: 101759-72-2

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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: C10H19NO5
Molecular weight: 233.3

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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-N-甲基-L-苏氨酸 在 palladium 10% on activated carbon 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 mineral oil 为溶剂， 反应 40.75h， 生成 (2S,3R)-2-((tert-butoxycarbonyl)(methyl)amino)-3-methoxybutanoic acid
  参考文献：
  名称：

  血小板聚集抑制剂环状二肽YM-280193的全合成

  摘要：

  描述了YM-280193的第一个全合成，这是一种环状的二肽，可抑制ADP诱导的人血小板聚集。使用常规化学方法制备单体和二肽片段，然后通过Fmoc-固相肽合成（Fmoc-SPPS）进行组装。一种新型的半烷基树脂上的双烷基化消除后期方法被用来引入非天然的N-甲基脱氢丙氨酸部分。最后一步涉及在受阻碍的非天然N，O-二甲基苏氨酸和β-羟基亮氨酸残基之间进行关键的大内酰胺化反应。

  DOI：

  10.1021/ol503507g

文献信息

• Structure-guided optimization and mechanistic study of a class of quinazolinone-threonine hybrids as antibacterial ThrRS inhibitors
  作者：Junsong Guo、Bingyi Chen、Ying Yu、Bao Cheng、Yingchen Ju、Jieyu Tang、Zhengjun Cai、Qiong Gu、Jun Xu、Huihao Zhou

  DOI：10.1016/j.ejmech.2020.112848

  日期：2020.12

  SeThrRS-8g complex revealed that 8g induced a bended conformation for Met332 by forming hydrophobic interactions, which better mimicked the binding of tRNAThr to ThrRS. Moreover, the inhibitory potency of 8g was less impaired than a reported ATP competitive inhibitor at high concentrations of ATP, supporting our hypothesis that tRNA site inhibitors are likely superior to ATP site inhibitors in vivo,

  氨酰基-tRNA合成酶（aaRSs）由于其在蛋白质翻译中的重要作用而成为一类有吸引力的抗菌药物靶标。虽然大多数传统的aaRS抑制剂都靶向底物氨基酸和/或ATP的结合口袋，但我们最近开发了一类新型tRNA-氨基酸双位抑制剂，包括抑制剂3（（2 S，3 R）-2-amino- N -（（E）-4-（6,7-dichloro-4-oxoquinazolin-3（4 H）-yl）but-2-en-1-yl）-3-hydroxybutanamide）反对苏氨酸tRNA合成酶（ThrRS） 。在此，通过肠沙门氏菌ThrRS（Se）的晶体结构分析了这些抑制剂的结合模式和构效关系（SARs）。ThrRS）与其中三个复杂。基于共晶体结构，设计并合成了十二种喹唑啉酮-苏氨酸杂化物，并评估了它们的亲和力，酶抑制活性和细胞效能。最好的衍生物8g的K d值为0.40μM，对Se ThrRS的IC 50值为0.50μ
• Studies on neurokinin antagonists. 2. Design and structure-activity relationships of novel tripeptide substance P antagonists, N.alpha.-[N.alpha.-(N.alpha.-acetyl-L-threonyl)-N1-formyl-D-tryptophyl]-N-methyl-N-(phenylmethyl)-L-phenylalaninamide and its related compounds
  作者：Daijiro Hagiwara、Hiroshi Miyake、Hiroshi Morimoto、Masako Murai、Takashi Fujii、Masaaki Matsuo

  DOI：10.1021/jm00095a013

  日期：1992.8

  terms of potency and stability. Subsequent modification of the amino terminal into N alpha-acetyl-L-threonine led to the most potent compound, N alpha-[N alpha-(N alpha-acetyl-L-threonyl)-N1-formyl-D-tryptophyl]-N- methyl-N-(phenylmethyl)-L-phenylalaninamide [Ac-Thr-D-Trp(CHO)-Phe-NMeBzl (5a, FR113680)]. This compound 5a potently blocked 3H-SP binding to guinea pig lung membranes with IC50 of (5.8 +/-

  继续研究先前报道的新型三肽SP拮抗剂Nα-[Nα-[Nα-（叔丁氧基羰基）谷氨酰胺基] -N1-甲酰基-D-色氨酸]苯丙氨酸苄酯[Boc-Gln- D-Trp-（CHO）-Phe-OBzl（1）]在本文中描述。我们最初研究了豚鼠血浆和肝脏匀浆中1的稳定性，以阐明结构中最不稳定的部分。结果表明，苄基酯部分易于水解以产生惰性酸类似物。因此，我们搜索了对水解酶更具抗性的苄基酯替代物。该方法发现了等价酰胺结构，N-甲基-N-（苯甲基）酰胺，其效力和稳定性均合适。随后将氨基末端修饰成Nα-乙酰基-L-苏氨酸导致了最有效的化合物Nα-[Nα-（Nα-乙酰基-L-苏氨酸）-N1-甲酰基-D-色氨酸] -N -甲基-N-（苯甲基）-L-苯丙氨酰胺[Ac-Thr-D-Trp（CHO）-Phe-NMeBzl（5a，FR113680）]。该化合物5a有效阻断3H-SP与豚鼠肺膜的结合，IC50为（5.8 +/-
• Marastoni; Salvadori; Balboni, Arzneimittel-Forschung/Drug Research, 1989, vol. 39, # 8, p. 926 - 928
  作者：Marastoni、Salvadori、Balboni、Spisani、Gavioli、Traniello、Tomatis

  DOI：——

  日期：——
• Discovery of ASP5286: A novel non-immunosuppressive cyclophilin inhibitor for the treatment of HCV
  作者：Takuya Makino、Seiji Yoshimura、Masahiro Neya、Toshio Yamanaka、Masae Sawada、Eisaku Tsujii、David Barrett

  DOI：10.1016/j.bmcl.2020.127308

  日期：2020.8

  Evidence indicates that hepatitis C virus (HCV) utilizes cellular cyclophilin proteins in its replication, and cyclophilin inhibitors represent a new class of anti-HCV agents. We have established an efficient synthetic methodology to generate FR901459 derivatives via N, O-acyl migration reaction while avoiding total synthesis. Through a detailed structure-activity relationship study, we improved anti-HCV activity while decreasing immunosuppressive activity. Additionally, we discovered the importance of substitution at the 3 position for not only improving anti-HCV activity but also pharmacokinetic profile. Finally, by striking an appropriate balance between potency, solubility, and permeability, we discovered ASP5286 (13) as a potential clinical candidate for anti-HCV therapy.
• AMINO ACID GENERATOR AND POLYSILOXANE COMPOSITION CONTAINING THE SAME
  申请人：Kato Taku

  公开号：US20110073977A1

  公开（公告）日：2011-03-31

  There is provided an amino acid generator comprising a protecting group for an amino group that is eliminated to generate an amino acid, and a coating film forming composition using the amino acid generator and a polysiloxane composition containing the amino acid generator. A coating film forming composition comprising: a component (A): an amino acid generator comprising a protecting group that is eliminated to generate an amino acid, which is a compound of Formula (1): D-A (1) where D is a protecting group for an amino group, and A is an organic group remaining after subtracting hydrogen atoms from an amino group of an amino acid; a component (B): a hydrolyzable silane, a hydrolysis product thereof, a hydrolysis-condensation product thereof, or a mixture thereof; and a component (C): a solvent.