甘氨酰-甘氨酰-L-亮氨酸 | 14857-82-0

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 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: 甘氨酰-甘氨酰-L-亮氨酸
• 中文别名: L-甘-甘-白三肽
• 英文名称: glycylglycyl-(L)-leucine
• 英文别名: glycyl-glycyl-L-leucine；Glycylglycyl-L-leucine；glycyl-glycyl-leucine；Gly-Gly-l-Leu；Gly-Gly-Leu；GGL；(2S)-2-[[2-[(2-aminoacetyl)amino]acetyl]amino]-4-methylpentanoic acid
• CAS: 14857-82-0
• 化学式: C₁₀H₁₉N₃O₄
• mdl: MFCD00067447
• 分子量: 245.279
• InChiKey: XPJBQTCXPJNIFE-ZETCQYMHSA-N

物化性质

• 熔点：
  195-198 °C (decomp)
• 沸点：
  573.7±45.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  126
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• WGK Germany：
  3
• 海关编码：
  2924199090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H317,H319

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Gly-gly-leu
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: Gly-gly-leu
CAS number: 14857-82-0

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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, 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: C10H19N3O4
Molecular weight: 245.3

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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：

  甘氨酰-甘氨酰-L-亮氨酸 、 N-乙酰-L-酪氨酸乙酯 在 pitrilysin 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以68.5%的产率得到Ac-Tyr-Gly-Gly-Leu
  参考文献：
  名称：

  Cerovsky, Vaclav; Martinek, Karel, Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 7, p. 2027 - 2041

  摘要：

  DOI：
• 作为产物：
  描述：

  N-[N-(N-benzyloxycarbonyl-glycyl)-glycyl]-L-leucine methyl ester 在 sodium hydroxide 作用下， 生成 甘氨酰-甘氨酰-L-亮氨酸
  参考文献：
  名称：

  Fruton; Smith; Driscoll, Journal of Biological Chemistry, 1948, vol. 173, p. 457,467

  摘要：

  DOI：

文献信息

• Linear energy correlations and failures in the low-energy tandem mass spectra of protonatedN-benzoylated tripeptides: Tools for probing mechanisms of CAD processes
  作者：Daniel G. Morgan、Maurice M. Bursey

  DOI：10.1002/jms.1190300410

  日期：1995.4

  The backbone cleavages for three series of protonated N-benzoyl tripeptide ions were studied in a hybrid tandem mass spectrometer: (i) benzoyl-Gly-Gly-Xxx, where Xxx = Gly, Ala, Val, Leu, Ile, Phe, Tyr, Met, Glu, Pro and Trp, (ii) benzoyl-Gly-Xxx-Gly, where Xxx = Gly, Ala, Leu, Phe, Tyr, Met and Trp, and (iii) benzoyl-Xxx-Gly-Gly, where Xxx = Gly, Ala, Val, Leu, Ile, Phe, Tyr, Met, Pro and Trp. C-Terminal y-type ions and N-terminal a- and b-type ions were noted in all three cases. For benzoyl-Gly-Gly-Xxx, a linear relationship between log (y1/b2) and the proton affinity of the C-terminal amino acid substituents was found: as the proton affinity of the C-terminal residue increases, the fraction of y1 ion formation increases. A similar relationship was noted for the benzoyl-Xxx-Gly-Gly tripeptides between log (y2/b1) and the proton affinity of the N-terminal amino acid substituent: as the proton affinity of the N-terminal residue increases, the fraction of b1 ion formation increases. For the series benzoyl-Gly-Xxx-Gly, these relationships did not hold true. These observations point to similar reaction pathways throughout the benzoyl-Gly-Gly-Xxx series and also similar pathways throughout the benzoyl-Xxx-Gly-Gly, but pathways that are substituent dependent for benzoyl-Gly-Xxx-Gly. The increased correlation coefficients for benzoyl-Gly-Gly-Xxx and benzoyl-Xxx-Gly-Gly when compared with the free tripeptides, suggest that fewer interfering competitive reactions exist, as fewer possibilities for internal hydrogen bonding exist in the N-benzoyl derivatives versus the free compounds.

  在一台混合串联质谱仪上，研究了三种系列的质子化N-苯甲酰三肽离子的骨架断裂：（i）苯甲酰-Gly-Gly-Xxx，其中Xxx = Gly、Ala、Val、Leu、Ile、Phe、Tyr、Met、Glu、Pro和Trp，（ii）苯甲酰-Gly-Xxx-Gly，其中Xxx = Gly、Ala、Leu、Phe、Tyr、Met和Trp，以及（iii）苯甲酰-Xxx-Gly-Gly，其中Xxx = Gly、Ala、Val、Leu、Ile、Phe、Tyr、Met、Pro和Trp。在所有三种情况下，都观察到了C端y型离子和N端a型及b型离子。对于苯甲酰-Gly-Gly-Xxx，发现log（y1/b2）与C端氨基酸取代基的质子亲和力之间存在线性关系：随着C端残基的质子亲和力增加，y1离子的形成分数增加。对于苯甲酰-Xxx-Gly-Gly三肽，log（y2/b1）与N端氨基酸取代基的质子亲和力之间存在类似的关系：随着N端残基的质子亲和力增加，b1离子的形成分数增加。对于苯甲酰-Gly-Xxx-Gly系列，这些关系并不成立。这些观察结果表明，在苯甲酰-Gly-Gly-Xxx系列和苯甲酰-Xxx-Gly-Gly系列中存在类似的反应途径，但对于苯甲酰-Gly-Xxx-Gly，途径依赖于取代基。与自由三肽相比，苯甲酰-Gly-Gly-Xxx和苯甲酰-Xxx-Gly-Gly的相关系数增加，表明存在的干扰竞争反应较少，因为在N-苯甲酰衍生物中内部氢键的可能性比自由化合物少。
• Sequence‐Specific Oxidative Degradation of Tripeptides by a Cobalt( <scp>III</scp> ) Complex Containing a Terpyridine Ligand
  作者：Koichiro Jitsukawa、Hiroshi Takahashi、Ryoji Hyuga、Hidekazu Arii、Hideki Masuda

  DOI：10.1002/ejic.200400261

  日期：2004.10

  intermediate for g′l on the basis of time-dependent HPLC analyses. NMR investigation of other tripeptides [βala-gly-leu (2), gly-gly-phe (3), and gly-gly-ala (4)] containing a bulky C-terminal aliphatic side chain indicated the formation of the corresponding oxidation complexes. On the other hand, peptides containing a C-terminal glycine residue [gly-gly-gly (5) and phe-gly-gly (6)] or an N-2 β-alanine

  使用三元钴 (III) 复合物对由脂肪族氨基酸组成的寡肽进行序列特异性氧化降解。在有氧条件下，[Co(CO3)(OH)(terpy)] 和等摩尔量的三肽在 40 °C、pH 8.5 下反应，得到两个带水的组分带（a 和 b），然后是两个带（c 和 d） ) 与 NaCl 溶液，分别在柱分离后。在gly-gly-leu (ggl, 1), [Co(gg'l)(terpy)] [1a, gg'l = glyyl(2-oxoglycyl)leucine], [Co(g'l)( terpy)] [1b, g'l = N-(2-oxoglycyl)leucine]、[Co(ggl)(terpy)]+ (1c) 和 [Co(terpy)2]3+ (1d)。主要产物 1c 的晶体结构表明起始 ggl 配体被裂解得到双酰胺化合物 g'l，这可能是由于 N-末端甘氨酸的丢失和 N-2 甘氨酸残基的 α-碳的
• Label-assisted laser desorption/ionization mass spectrometry (LA-LDI-MS): use of pyrene aldehyde for detection of biogenic amines, amino acids and peptides
  作者：Arundhoti Mandal、Amit K. Das、Amit Basak

  DOI：10.1039/c5ra20678b

  日期：——

  flight (TOF) mass spectrometric measurement. By excluding the external matrix, the mass spectrum becomes much cleaner being free of matrix related peaks and noises. Peaks corresponding to compounds/complexes formed between the analytes and the label are mostly seen in the spectrum. In this paper we report a LA-LDI mass spectrometry based method for detection of amines, including the ones ubiquitous to

  标记辅助激光解吸/电离（LA-LDI）技术最近已应用于通过飞行时间（TOF）质谱测量来检测小分子。通过排除外部基质，质谱变得更加干净，没有基质相关的峰和噪声。对应于分析物和标记物之间形成的化合物/复合物的峰通常在光谱中可见。在本文中，我们报告了一种基于LA-LDI质谱法的胺检测方法，其中包括使用1-py甲醛作为LDI标签的生物样品中普遍存在的胺，如生物胺，氨基酸，二肽和三肽。
• SOLOMONAMIDE ANALOGUE COMPOUNDS, PHARMACEUTICALS CONTAINING SOLOMONAMIDE ANALOGUE COMPOUNDS, AND PROCESSES FOR THE PREPARATION THEREOF
  申请人：COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH

  公开号：US20150291659A1

  公开（公告）日：2015-10-15

  Solomanamide analogues of Formula-I having anti-inflammatory activity, and viable synthetic routes for the preparation of such analogues, including the synthesis of macrocyclic core of Salomanamide analogues. The Solomanamide analogues of Formula-I or their pharmaceutical salt may be provided in a pharmaceutical composition and administered in an effective amount for the treatment of inflammation and/or pain.

  公式I的Solomanamide类似物具有抗炎活性，并且具有制备这种类似物的可行合成路线，包括制备Salomanamide类似物的大环核心的合成。公式I的Solomanamide类似物或其药物盐可以在药物组合物中提供，并以有效剂量用于治疗炎症和/或疼痛。
• C-TERMINUS AMIDATION ENZYME COMPOSITION, PROCESS FOR ITS PREPARATION AND ITS USE
  申请人：SHISEIDO COMPANY LIMITED

  公开号：EP0447547A1

  公开（公告）日：1991-09-25

  A C-terminus amidation enzyme composition of serum or blood plasma origin, which acts on a C-terminus glycine adduct represented by formula (I) (wherein A represents a residue other than α-amino or imino group and α-carboxyl group of a natural α-amino acid origin, and X represents a hydrogen atom or a residue of an amino acid derivative bound to the N atom via a carbonyl group) to produce a C-terminus amidation product represented by formula (II) (wherein A and X are as defined above) and glyoxylic acid, is disclosed. A process for preparing the composition and its use are also disclosed.

  一种来源于血清或血浆的 C-端酰胺化酶组合物，它作用于式(I)代表的 C-端甘氨酸加合物（其中 A 代表除天然 α-氨基酸来源的 α-氨基或亚胺基和 α-羧基以外的残基），X 代表氢原子或通过羰基与 N 原子结合的氨基酸衍生物残基、和 X 代表氢原子或通过羰基与 N 原子结合的氨基酸衍生物残基），以产生由式 (II) 代表的 C 端酰胺化产物（其中 A 和 X 如上定义）和乙醛酸。还公开了制备该组合物的工艺及其用途。

表征谱图