N-芴甲氧羰基-D-别异亮氨酸 | 118904-37-3

• 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-芴甲氧羰基-D-别异亮氨酸
• 中文别名: Fmoc-D-别异亮氨酸；FMOC-D-别异亮氨酸
• 英文名称: N-(9-Fluorenylmethoxycarbonyl)-D-alloisoleucine
• 英文别名: Fmoc-D-allo-Ile-OH；Fmoc-D-allo-Ile；Fmoc-D-alloisoleucine；FMOC-D-allo-Isoleucine；(2R,3S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylpentanoic acid
• CAS: 118904-37-3
• 化学式: C₂₁H₂₃NO₄
• 分子量: 353.418
• InChiKey: QXVFEIPAZSXRGM-ORAYPTAESA-N

物化性质

• 沸点：
  559.8±33.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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：
  密封，在温室中保存

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Fmoc-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: Fmoc-D-Allo-Ile-OH
CAS number: 118904-37-3

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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, refrigerated.
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: C21H23NO4
Molecular weight: 353.4

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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

制备方法与用途

Fmoc-D-Allo-Ile-OH是一种异亮氨酸衍生物。

反应信息

• 作为反应物：
  描述：

  N-芴甲氧羰基-D-别异亮氨酸 在 盐酸 、 sodium hydroxide 、 氯化亚砜 、 水 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 30.0h， 生成 (3S,4R,5S)-isostatine
  参考文献：
  名称：

  双嘧达明的全合成-1.肽环1的合成

  摘要：

  二羟肌酐的23元肽环是在线性ω-氨基-五氟苯基酯的两相环化反应中形成的，产率为70％，无需高稀释度。（2 ，4 ）-2,5-二甲基-4-羟基-3-氧代己酸（HIP）和（3 ，4 ，5 ）-isostatine由三甲基硅烷丙二酸酯酰化合成。

  DOI：

  10.1016/0040-4039(88)85084-6
• 作为产物：
  描述：

  N-(9-Fluorenylmethoxycarbonyl)-D-alloisoleucine methyl ester 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 以90%的产率得到N-芴甲氧羰基-D-别异亮氨酸
  参考文献：
  名称：

  Total Synthesis of the Didemnins; III. - Synthesis of Protected (2R,3S)-Alloisoleucine and (3S,4R,5S)-Isostatine Derivatives - Amino Acids from Hydroxy Acids

  摘要：

  (2S,3S)-2-乙酰氧基-3-甲基戊酸（3）是通过L-异亮氨酸（2）制备的，保留构型率为96%。化合物3转化为光学纯的甲基D-全异亮氨酸盐酸盐（7），经过甲烷磺酸酯5和叠氮化合物6，产率为76%，反转率为99.9%。随后对7进行保护-皂化-活化反应，再与甲基三甲基硅基丙二酸锂烯醇盐反应并还原，得到(3S,4R,5S)-N-(9-芴甲氧基羰基)异亮氨酸（12）。(3S,4R,5S)-异亮氨酸是二氟氮碱1的特征单元。

  DOI：

  10.1055/s-1989-27404

文献信息

• Champacyclin, a New Cyclic Octapeptide from Streptomyces Strain C42 Isolated from the Baltic Sea
  作者：Alexander Pesic、Heike Baumann、Katrin Kleinschmidt、Paul Ensle、Jutta Wiese、Roderich Süssmuth、Johannes Imhoff

  DOI：10.3390/md11124834

  日期：——

  champacyclin (1a) present in all three strains. Herein, we report on the isolation, structure elucidation and determination of the absolute stereochemistry of this isoleucine/leucine (Ile/Leu = Xle) rich cyclic octapeptide champacyclin (1a). As 2D nuclear magnetic resonance (NMR) spectroscopy could not fully resolve the structure of (1a), additional information on sequence and configuration of stereocenters

  从哥特兰深海（波罗的海）、乌拉尼亚盆地（地中海东部）和基尔湾（波罗的海）的海洋沉积物中分离出新的 Streptomyces champavatii 分离株。这些分离株产生了几种寡肽次生代谢物，包括所有三种菌株中都存在的新八肽尚帕环素 (1a)。在此，我们报告了这种富含异亮氨酸/亮氨酸 (Ile/Leu = Xle) 的环状八肽香槟环素 (1a) 的绝对立体化学的分离、结构解析和测定。由于二维核磁共振 (NMR) 光谱无法完全解析 (1a) 的结构，因此通过多级质谱 (MSn) 研究、氨基酸分析、部分水解和随后的对映体分析采用气相色谱正化学电离/电子轰击质谱 (GC-PCI/EI-MS)，并与参考二肽进行比较。与选择性侧链环化衍生物 (2) 相比，通过固相肽合成 (SPPS) 证明了 (1a) 的头对尾环化。尚帕环素 (1a) 可能由非核糖体肽合成酶 (NRPS) 合成，因为其 (D)-氨基
• Anti-angiogenic compounds
  申请人：Bradshaw W. Curt

  公开号：US20060205670A1

  公开（公告）日：2006-09-14

  The present invention provides AA targeting compounds which comprise AA targeting agent-linker conjugates which are linked to a combining site of an antibody. Various uses of the compounds are provided, including methods to treat disorders connected to abnormal angiogenesis.

  本发明提供了包括与抗体的结合位点连接的AA靶向剂-连接剂共轭物的AA靶向化合物。提供了化合物的各种用途，包括治疗与异常血管生成相关的疾病的方法。
• Solid‐Phase Total Synthesis of Yaku'amide B Enabled by Traceless Staudinger Ligation
  作者：Hiroaki Itoh、Kensuke Miura、Koichi Kamiya、Tomoya Yamashita、Masayuki Inoue

  DOI：10.1002/anie.201916517

  日期：2020.3.9

  solid-phase strategy for total synthesis of the peptidic natural product yaku'amide B (1), which exhibits antiproliferative activity against various cancer cells. Its linear tridecapeptide sequence bears four β,β-dialkylated α,β-dehydroamino acid residues and is capped with an N-terminal acyl group (NTA) and a C-terminal amine (CTA). To realize the Fmoc-based solid-phase synthesis of this complex structure

  我们报告了肽天然产物雅库酰胺B（1）的全合成的固相策略，它对各种癌细胞都具有抗增殖活性。它的线性三肽序列带有四个β，β-二烷基化的α，β-脱氢氨基酸残基，并被N末端酰基（NTA）和C末端胺（CTA）封端。为了实现这种复杂结构的基于Fmoc的固相合成，我们开发了用于酰胺形成，酰胺脱保护和C末端修饰的新方法。首先，无痕的施陶丁格连接使空间阻碍的烯基叠氮化物与新设计的膦酚酚酯之间形成酰胺。其次，Eu（OTf）3的使用导致化学选择性去除了酰胺Boc基团，而没有分离树脂接头。最后，
• “O-Acyl isopeptide method” for peptide synthesis: synthesis of forty kinds of “O-acyl isodipeptide unit” Boc-Ser/Thr(Fmoc-Xaa)-OH
  作者：Taku Yoshiya、Atsuhiko Taniguchi、Youhei Sohma、Fukue Fukao、Setsuko Nakamura、Naoko Abe、Nui Ito、Mariusz Skwarczynski、Tooru Kimura、Yoshio Hayashi、Yoshiaki Kiso

  DOI：10.1039/b702284k

  日期：——

  The O-acyl isopeptide method has recently received attention as an efficient synthetic method for peptides. Herein, forty kinds of "O-acyl isodipeptide unit" Boc-Ser/Thr(Fmoc-Xaa)-OH (1-40) were effectively synthesized in two-steps without epimerization. The O-acyl isodipeptide units are important building blocks to enable the routine use of the O-acyl isopeptide method.

  作为有效的肽合成方法，O-酰基异肽方法最近受到关注。在此，两步法有效地合成了40种“ O-酰基异二肽单元” Boc-Ser / Thr（Fmoc-Xaa）-OH（1-40），而没有差向异构化。O-酰基异二肽单元是重要的组成部分，可以常规使用O-酰基异肽方法。
• Studies on tridecaptin B₁, a lipopeptide with activity against multidrug resistant Gram-negative bacteria
  作者：Stephen A. Cochrane、Christopher T. Lohans、Marco J. van Belkum、Manon A. Bels、John C. Vederas

  DOI：10.1039/c5ob00780a

  日期：——

  Tridecaptin B₁is a new lipopeptide with activity against Gram-negative bacteria.

  Tridecaptin B₁是一种针对革兰氏阴性细菌活性的新脂肽。