Gramicidin A | 1405-97-6

• 物质功能分类: 原料药 - 人工合成抗感染类药 - 抗真菌类药
• 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
• 英文名称: Gramicidin A
• 英文别名: (2R)-N-[(2S)-1-hydroxy-1-[(2R)-1-hydroxy-1-[(2S)-1-hydroxy-1-[(2R)-1-hydroxy-1-[(2S)-1-hydroxy-1-[(2R)-1-hydroxy-1-[(2S)-1-hydroxy-1-[(2R)-1-hydroxy-1-[(2S)-1-hydroxy-1-[(2R)-1-hydroxy-1-[(2S)-1-hydroxy-1-(2-hydroxyethylimino)-3-(1H-indol-3-yl)propan-2-yl]imino-4-methylpentan-2-yl]imino-3-(1H-indol-3-yl)propan-2-yl]imino-4-methylpentan-2-yl]imino-3-(1H-indol-3-yl)propan-2-yl]imino-4-methylpentan-2-yl]imino-3-(1H-indol-3-yl)propan-2-yl]imino-3-methylbutan-2-yl]imino-3-methylbutan-2-yl]imino-3-methylbutan-2-yl]iminopropan-2-yl]-2-[[(2S)-1-hydroxy-2-[[1-hydroxy-2-[[(2S)-1-hydroxy-2-(hydroxymethylideneamino)-3-methylbutylidene]amino]ethylidene]amino]propylidene]amino]-4-methylpentanimidic acid
• CAS: 1405-97-6
• 化学式: C₉₉H₁₄₀N₂₀O₁₇
• 分子量: 1882.32
• InChiKey: ZWCXYZRRTRDGQE-LUPIJMBPSA-N

物化性质

• 熔点：
  229-230℃
• 溶解度：
  几乎不溶于水，溶于甲醇，微溶于乙醇

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  136
• 可旋转键数：
  52
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  549
• 氢给体数：
  21
• 氢受体数：
  17

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S22,S24/25,S26,S36
• 危险类别码：
  R20/21,R36/37/38
• WGK Germany：
  3
• 海关编码：
  2941906000
• 储存条件：
  2-8°C

SDS

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Section 1. Chemical Product and Company Identification
Gramicidin D Catalog
G1171, G1032
Common Name/
Number(s).
Trade Name
CAS# 1393-88-0
Manufacturer
RTECS MD8440000
SPECTRUM CHEMICAL MFG. CORP.
TSCA TSCA 8(b) inventory: No
products were found.
Commercial Name(s) Not available.
CI# Not available.
Synonym Not available.
IN CASE OF EMERGENCY
Not available.
Chemical Name
Chemical Family Not available. CALL [phone]
Not available.
Chemical Formula
SPECTRUM CHEMICAL MFG. CORP.

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Section 2.Composition and Information on Ingredients
Exposure Limits
TWA (mg/m3) STEL (mg/m3) CEIL (mg/m3)
Name CAS # % by Weight
1) Gramicidin D 1393-88-0 100
Toxicological Data Not applicable.
on Ingredients

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Section 3. Hazards Identification
Potential Acute Health Effects Hazardous in case of ingestion. Slightly hazardous in case of skin contact (irritant), of eye contact (irritant), of
inhalation.
Potential Chronic Health Hazardous in case of ingestion.
Slightly hazardous in case of skin contact (irritant), of eye contact (irritant), of inhalation.
Effects
CARCINOGENIC EFFECTS: Not available.
MUTAGENIC EFFECTS: Not available.
TERATOGENIC EFFECTS: Not available.
DEVELOPMENTAL TOXICITY: Not available.
Gramicidin D

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Section 4. First Aid Measures
Eye Contact No known effect on eye contact, rinse with water for a few minutes.
Skin Contact After contact with skin, wash immediately with plenty of water. Gently and thoroughly wash the contaminated skin
with running water and non-abrasive soap. Be particularly careful to clean folds, crevices, creases and groin.
Cover the irritated skin with an emollient. If irritation persists, seek medical attention. Wash contaminated
clothing before reusing.
Serious Skin Contact Not available.
Inhalation Allow the victim to rest in a well ventilated area. Seek immediate medical attention.
Serious Inhalation Not available.
Ingestion Do not induce vomiting. Loosen tight clothing such as a collar, tie, belt or waistband. If the victim is not
breathing, perform mouth-to-mouth resuscitation. Seek immediate medical attention.
Serious Ingestion Not available.

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Section 5. Fire and Explosion Data
Flammability of the Product May be combustible at high temperature.
Auto-Ignition Temperature Not available.
Flash Points Not available.
Flammable Limits Not available.
Not available.
Products of Combustion
Fire Hazards in Presence of Not available.
Various Substances
Explosion Hazards in Presence Risks of explosion of the product in presence of mechanical impact: Not available.
of Various Substances Risks of explosion of the product in presence of static discharge: Not available.
Fire Fighting Media SMALL FIRE: Use DRY chemical powder.
and Instructions LARGE FIRE: Use water spray, fog or foam. Do not use water jet.
Special Remarks on Not available.
Fire Hazards
Special Remarks on Explosion Not available.
Hazards

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Section 6. Accidental Release Measures
Small Spill Use appropriate tools to put the spilled solid in a convenient waste disposal container. Finish cleaning by
spreading water on the contaminated surface and dispose of according to local and regional authority
requirements.
Large Spill
Use a shovel to put the material into a convenient waste disposal container. Finish cleaning by spreading water
on the contaminated surface and allow to evacuate through the sanitary system.
Gramicidin D

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Section 7. Handling and Storage
Precautions Keep away from heat. Keep away from sources of ignition. Empty containers pose a fire risk, evaporate the
residue under a fume hood. Ground all equipment containing material. Do not breathe dust.
Storage Keep container dry. Keep in a cool place. Ground all equipment containing material. Keep container tightly
closed. Keep in a cool, well-ventilated place. Combustible materials should be stored away from extreme heat
and away from strong oxidizing agents.

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Section 8. Exposure Controls/Personal Protection
Engineering Controls Use process enclosures, local exhaust ventilation, or other engineering controls to keep airborne levels below
recommended exposure limits. If user operations generate dust, fume or mist, use ventilation to keep exposure to
airborne contaminants below the exposure limit.
Personal Protection Safety glasses. Lab coat. Dust respirator. Be sure to use an approved/certified respirator or equivalent. Gloves.
Personal Protection in Case of Splash goggles. Full suit. Dust respirator. Boots. Gloves. A self contained breathing apparatus should be used
a Large Spill to avoid inhalation of the product. Suggested protective clothing might not be sufficient; consult a specialist
BEFORE handling this product.
Exposure Limits Not available.

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Section 9. Physical and Chemical Properties
Physical state and appearance Solid. (Solid crystalline powder.) Odorless.
Odor
Taste Not available.
Molecular Weight Not available.
Color White.
pH (1% soln/water) Not available.
Boiling Point Decomposes.
Melting Point 229°C (444.2°F)
Critical Temperature Not available.
Not available.
Specific Gravity
Vapor Pressure Not applicable.
Not available.
Vapor Density
Volatility Not available.
Not available.
Odor Threshold
Water/Oil Dist. Coeff. Not available.
Ionicity (in Water) Not available.
Not available.
Dispersion Properties
Solubility Not available.

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Section 10. Stability and Reactivity Data
Stability The product is stable.
Instability Temperature Not available.
Conditions of Instability Not available.
Incompatibility with various Not available.
substances
Corrosivity Non-corrosive in presence of glass.
Gramicidin D
Not available.
Special Remarks on
Reactivity
Not available.
Special Remarks on
Corrosivity
Polymerization No.

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Section 11. Toxicological Information
Routes of Entry Ingestion.
Toxicity to Animals LD50: Not available.
LC50: Not available.
Chronic Effects on Humans Not available.
Other Toxic Effects on
Hazardous in case of ingestion.
Humans Slightly hazardous in case of skin contact (irritant), of inhalation.
Special Remarks on
Not available.
Toxicity to Animals
Special Remarks on Not available.
Chronic Effects on Humans
Special Remarks on other Not available.
Toxic Effects on Humans

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Section 12. Ecological Information
Ecotoxicity Not available.
Not available.
BOD5 and COD
Possibly hazardous short term degradation products are not likely. However, long term degradation products may
Products of Biodegradation
arise.
Toxicity of the Products The products of degradation are more toxic.
of Biodegradation
Special Remarks on the Not available.
Products of Biodegradation

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Section 13. Disposal Considerations
Waste Disposal

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Section 14. Transport Information
DOT Classification Not a DOT controlled material (United States).
Identification Not applicable.
Not applicable.
Special Provisions for
Transport
DOT (Pictograms)
Gramicidin D

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Section 15. Other Regulatory Information and Pictograms
TSCA 8(b) inventory: No products were found.
Federal and State
Regulations
California
Proposition 65
Warnings
Other Regulations Not available..
WHMIS (Canada) Not controlled under WHMIS (Canada).
Other Classifications
DSCL (EEC) This product is not classified according
to the EU regulations.
Health Hazard
HMIS (U.S.A.) 1 National Fire Protection
1 Flammability
1 Association (U.S.A.)
Fire Hazard
1 0 Reactivity
Health
Reactivity
0
Specific hazard
Personal Protection
E
WHMIS (Canada)
(Pictograms)
DSCL (Europe)
(Pictograms)
TDG (Canada)
(Pictograms)
ADR (Europe)
(Pictograms)
Protective Equipment
Gloves.
Lab coat.
Dust respirator. Be sure to use an
approved/certified respirator or
equivalent.
Safety glasses.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性

Gramicidin 是一种抗菌肽，能够组装成膜中的通道并增加其对阳离子的渗透性。

靶点

• 细菌：Gramicidin 主要针对革兰氏阳性菌如金黄色葡萄球菌（S. aureus）表现出活性，而对大肠杆菌（E. coli）和酿酒酵母（S. cerevisiae）的抗菌效果较差。

体外研究

• Gramicidin 在低浓度下对金黄色葡萄球菌具有微杀菌作用，并且这些浓度不会对酿酒酵母造成毒性。然而，Gramicidin 对大肠杆菌和酿酒酵母的活性较低，在不同浓度下的存活率差异不大。

参考质量标准

• 外观性状：白色粉末
• 纯度 (HPLC)：≥98.0%
• 醋酸根含量：≤12.0%
• 水分含量：≤8.0%
• 肽含量：≥80.0%
• 内毒素：≤50EU/mg
• 氨基酸组成分析：±10%

反应信息

• 作为反应物：
  描述：

  Gramicidin A 在 氘代甲醇-d 作用下， 反应 24.0h， 生成 2-(3,5-bis((bis(pyridin-2-ylmethyl)amino)methyl)phenoxy)-N-(2-mercaptoethyl)acetamide
  参考文献：
  名称：

  Gramicidin A的溶剂依赖性自组装/拆解和构象异构体偏好性的实验研究

  摘要：

  使用组合技术，即电喷雾电离-离子迁移率-质谱（IM-MS），碰撞诱导解离等技术，研究了自组装/拆解动力学的溶剂依赖性以及短杆菌肽A（GA）二聚体的构象异构体偏好（CID）和氢/氘交换（HDX）-MS。IM-MS测量表明，可能存在三种不同的GA二聚体，分别检测为钠离子加成离子[2GA + 2Na] 2+，它们被指定为平行β螺旋，反平行β螺旋和头对头二聚体。二聚体离子的单体化动力学和平衡丰度取决于溶剂的极性。反平行β-螺旋是在极性较小的溶剂中热力学上优选的物质。HDX测量和中间体配合物的碰撞诱导解离（CID）证实了具有强分子间氢键的保护良好的二聚体几何结构。这种组合的IM-HDX-CID方法提供了低介电溶液中GA自组装/分解的全面视图，显示了其在解决溶液相蛋白质自组装/分解动力学方面的潜在效用，并同时提供了多聚体的结构信息时间。

  DOI：

  10.1021/ac401370t
• 作为产物：
  描述：

  在 三异丙基硅烷 、 水 、 三氟乙酸 、 苯酚 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 Gramicidin A
  参考文献：
  名称：

  Polar Groups in Membrane Channels: Consequences of Replacing Alanines with Serines in Membrane-Spanning Gramicidin Channels

  摘要：

  To explore the consequences of burying polar, hydrogen-bonding hydroxyl groups within the hydrocarbon core of lipid bilayer membranes, we examined the structural and functional effects of alanine-to-serine substitutions in bilayer-spanning gramicidin channels. A native Ala was replaced by Ser at position 3 or 5 in the gramicidin A (gA) sequence: formyl-VG(2)A(3)LA(5)VVVWLWLWLW-ethanolamide (D-residues underlined). In the head-to-head dirners that form the conducting, membrane-spanning gA channels, these sequence positions are located near the lipid bilayer center (and subunit interface). The sequence substitutions at positions 3 and 5 were tested within the context of having either Gly or D-Ala at position 2, because D-Ala(2) causes the channel lifetimes to increase 3-fold relative to G1y2 [Mattice et al. (1995) Biochemistry 34, 6827]. Size-exclusion chromatograms and circular dichroism spectra show that the Ala -> Ser replacements are well tolerated and have little effect on channel structure. In planar bilayers, the Ser-substituted gramicidins form well-defined channels, with cation conductances that are similar to 60% of those of the reference channels. The Sersubstituted channels are structurally equivalent to native gramicidin channels, as demonstrated by the formation of heterodimeric channels between a Ser-containing subunit and a native gramicidin subunit. These hybrid channels exhibit rectification, attributable to asymmetric placement of the single Ser hydroxyl group with respect to the bilayer center. Compared to the corresponding Ala-containing reference channels, the polar Ser residues decrease the analogues' channel-forming potency by 3 orders of magnitude, indicating a substantial energetic penalty (similar to 15 kJ/mol) for burying the polar Ser side chain in the bilayer hydrophobic core.

  DOI：

  10.1021/bi100857g

文献信息

• HIGH THROUGHPUT SCREEN FOR MEASURING MEMBRANE EFFECTS
  申请人：Ingolfsson Helgi I.

  公开号：US20120184450A1

  公开（公告）日：2012-07-19

  The invention relates to assays for measuring the effect of a inactive test substance on a lipid bilayer, kits for measuring the effects of test substances on lipid bilayers and an apparatus for performing a high through-put assay that measures the effect of test substances on a lipid bilayer.
• US8901042B2
  申请人：——

  公开号：US8901042B2

  公开（公告）日：2014-12-02
• Polar Groups in Membrane Channels: Consequences of Replacing Alanines with Serines in Membrane-Spanning Gramicidin Channels
  作者：Anna E. Daily、Jung H. Kim、Denise V. Greathouse、Olaf S. Andersen、Roger E. Koeppe

  DOI：10.1021/bi100857g

  日期：2010.8.17

  To explore the consequences of burying polar, hydrogen-bonding hydroxyl groups within the hydrocarbon core of lipid bilayer membranes, we examined the structural and functional effects of alanine-to-serine substitutions in bilayer-spanning gramicidin channels. A native Ala was replaced by Ser at position 3 or 5 in the gramicidin A (gA) sequence: formyl-VG(2)A(3)LA(5)VVVWLWLWLW-ethanolamide (D-residues underlined). In the head-to-head dirners that form the conducting, membrane-spanning gA channels, these sequence positions are located near the lipid bilayer center (and subunit interface). The sequence substitutions at positions 3 and 5 were tested within the context of having either Gly or D-Ala at position 2, because D-Ala(2) causes the channel lifetimes to increase 3-fold relative to G1y2 [Mattice et al. (1995) Biochemistry 34, 6827]. Size-exclusion chromatograms and circular dichroism spectra show that the Ala -> Ser replacements are well tolerated and have little effect on channel structure. In planar bilayers, the Ser-substituted gramicidins form well-defined channels, with cation conductances that are similar to 60% of those of the reference channels. The Sersubstituted channels are structurally equivalent to native gramicidin channels, as demonstrated by the formation of heterodimeric channels between a Ser-containing subunit and a native gramicidin subunit. These hybrid channels exhibit rectification, attributable to asymmetric placement of the single Ser hydroxyl group with respect to the bilayer center. Compared to the corresponding Ala-containing reference channels, the polar Ser residues decrease the analogues' channel-forming potency by 3 orders of magnitude, indicating a substantial energetic penalty (similar to 15 kJ/mol) for burying the polar Ser side chain in the bilayer hydrophobic core.
• An Experimental Study of the Solvent-Dependent Self-Assembly/Disassembly and Conformer Preferences of Gramicidin A
  作者：Liuxi Chen、Shu-Hua Chen、David H. Russell

  DOI：10.1021/ac401370t

  日期：2013.8.20

  The solvent dependence of self-assembly/disassembly kinetics and conformer preferences of the gramicidin A (GA) dimer is investigated using a combination of techniques, viz., electrospray ionization–ion mobility–mass spectrometry (IM-MS), collision-induced dissociation (CID), and hydrogen/deuterium exchange (HDX)-MS. IM-MS measurements reveal that there are possibly three distinct GA dimeric species

  使用组合技术，即电喷雾电离-离子迁移率-质谱（IM-MS），碰撞诱导解离等技术，研究了自组装/拆解动力学的溶剂依赖性以及短杆菌肽A（GA）二聚体的构象异构体偏好（CID）和氢/氘交换（HDX）-MS。IM-MS测量表明，可能存在三种不同的GA二聚体，分别检测为钠离子加成离子[2GA + 2Na] 2+，它们被指定为平行β螺旋，反平行β螺旋和头对头二聚体。二聚体离子的单体化动力学和平衡丰度取决于溶剂的极性。反平行β-螺旋是在极性较小的溶剂中热力学上优选的物质。HDX测量和中间体配合物的碰撞诱导解离（CID）证实了具有强分子间氢键的保护良好的二聚体几何结构。这种组合的IM-HDX-CID方法提供了低介电溶液中GA自组装/分解的全面视图，显示了其在解决溶液相蛋白质自组装/分解动力学方面的潜在效用，并同时提供了多聚体的结构信息时间。