368020

Gramicidin A

from Bacillus brevis, ≥90% (HPLC), solid, ion channel-forming pentadecapeptide, Calbiochem^®

• Synonym(s): Gramicidin A, High Purity, Bacillus brevis, gA
• Empirical Formula (Hill Notation): C₉₉H₁₄₀N₂₀O₁₇
• CAS Number: 11029-61-1
• Molecular Weight: 1882.29
• UNSPSC Code: 51283112
• NACRES: NA.77
• MDL number: MFCD00466944
• Assay: ≥90% (HPLC)
• Form: solid
• Storage condition: OK to freeze

Properties

• Product Name: Gramicidin A, High Purity, Bacillus brevis, Gramicidin A, High Purity, Bacillus brevis, CAS 11029-61-1, is a naturally-occurring ion channel-forming pentadecapeptide. Causes K⁺/H⁺ exchange in mitochondria in a non-voltage dependent manner.
• Quality Segment: 100
• description: Merck USA index - 14, 4532
• assay: ≥90% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• impurities: <5% gC isomers (HPLC)
• color: white to off-white
• solubility: DMSO: 100 mg/mL
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: [nH]1c2c(c(c1)C[C@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC=O)C(C)C)C)CC(C)C)C)C(C)C)C(C)C)C(C)C)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](Cc7c8c([nH]c7)cccc8)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](Cc5c6c([nH]c5)c
• InChI: 1S/C99H140N20O17/c1-51(2)37-73(109-86(123)59(17)107-81(122)49-105-96(133)82(55(9)10)106-50-121)89(126)108-60(18)87(124)117-84(57(13)14)98(135)119-85(58(15)16)99(136)118-83(56(11)12)97(134)116-80(44-64-48-104-72-34-26-22-30-68(64)72)95(132)112-76(40-54(7)8)92(129)115-79(43-63-47-103-71-33-25-21-29-67(63)71)94(131)111-75(39-53(5)6)91(128)114-78(42-62-46-102-70-32-24-20-28-66(62)70)93(130)110-74(38-52(3)4)90(127)113-77(88(125)100-35-36-120)41-61-45-101-69-31-23-19-27-65(61)69/h19-34,45-48,50-60,73-80,82-85,101-104,120H,35-44,49H2,1-18H3,(H,100,125)(H,105,133)(H,106,121)(H,107,122)(H,108,126)(H,109,123)(H,110,130)(H,111,131)(H,112,132)(H,113,127)(H,114,128)(H,115,129)(H,116,134)(H,117,124)(H,118,136)(H,119,135)/t59-,60-,73+,74+,75+,76+,77-,78-,79-,80-,82-,83+,84+,85-/m0/s1
• InChI key: ZWCXYZRRTRDGQE-LUPIJMBPSA-N

Description

General description

Naturally occurring, ion channel-forming pentadecapeptide antibiotic that renders membranes permeable to protons and alkali metal ions. Causes red blood cell lysis at concentrations of 0.5-1.0 µg/ml. Gramicidin A causes K⁺/H⁺ exchange in mitochondria in a non-voltage dependent manner.

Naturally-occurring ion channel-forming pentadecapeptide. The association of two gA peptides causes the formation of a monovalent cation-selective ion channel. Causes K⁺/H⁺ exchange in mitochondria in a non-voltage dependent manner. Causes red blood cell lysis at 0.5-1.0 µg/ml.

Biochem/physiol Actions

Cell permeable: no

Primary Target
Causes the formation of a monovalent cation-selective ion channel

Product does not compete with ATP.

Reversible: no

Preparation Note

Following recosntituion, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

HCO-Val-Gly-Ala-D-Leu-Ala-D-Val-Val-D-Val-Trp-D-Leu-Trp-D-Leu-Trp-D-Leu-Trp-NHCH₂CH₂OH

Quigley, E.P., et al. 2000. J. Membr. Biol. 174,207.
Koeppe, R.E., et al. 1995. Biochemistry34, 9299.
Ketchem, R.R., et al. 1993. Science261, 1457.
Stankovic, C.J., et al. 1990. Anal. Biochem.184, 100.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Harmful (C)

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H302
• pcodes: P264 - P270 - P301 + P312 - P501
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable