Gramicidin A | B2967

Gramicidin A is a peptide component of gramicidin, an antibiotic mixture originally isolated from Bacillus brevis. Gramicidin A is a linear channel-forming ionophore pentadecapeptide that forms a hydrophilic membrane pore that permits the rapid passage of monovalent cations. Gramicidin A shows potent antibiotic activity against gram-positive bacteria by forming channels which cause Na+ influx, K+ efflux, osmotic swelling, and cell lysis.

Gramicidin A is a peptide component of gramicidin, an antibiotic mixture originally isolated from Bacillus brevis. Gramicidin A is a linear channel-forming ionophore pentadecapeptide that forms a hydrophilic membrane pore that permits the rapid passage of monovalent cations. Gramicidin A shows potent antibiotic activity against gram-positive bacteria by forming channels which cause Na+ influx, K+ efflux, osmotic swelling, and cell lysis.

B2967 | Gramicidin A DataSheet

Alternate Name/Synonyms: Valinegramicidin A; Valyl gramicidin A; (2R)-2-[[(2S)-2-[[2-[[(2S)-2-formamido-3-methylbutanoyl]amino]acetyl]amino]propanoyl]amino]-N-[(2S)-1- [[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-(2-hydroxyethylamino)-3- (1H-indol-3-yl)-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]- 4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)- 1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1- oxopropan-2-yl]-4-methylpentanamide

Appearance: Solid

Formulation:

CAS Number: 11029-61-1

Structure Available?: True

Peptide sequence: HCO-Val-Gly-Ala-D-Leu-Ala-D-Val-Val-D-Val-Trp-D-Leu-Trp-D-Leu-Trp-D-Leu-Trp-NHCH₂CH₂OH

Salt Form: false

Molecular Formula: C₉₉H₁₄₀N₂₀O₁₇

Molecular Weight: 1882.29

Cell-Permeable?: True

Purity: ≥90%

Solubilities: Soluble in ethanol and DMSO in 0

Handling: Do not take internally. Wear gloves and mask when handling the product! Avoid contact by all modes of exposure.

Country of Origin: USA

Tag Line: A channel-forming antibiotic

MDL Number:

PubChem CID: 16132269

SMILES: CC(C)CC(C(=O)NC(C)C(=O)NC(C(C)C)C(=O)NC(C(C)C)C(=O)NC(C(C)C)C(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CC(C)C)C(=O)NC(CC3=CNC4=CC=CC=C43)C(=O)NC(CC(C)C)C(=O)NC(CC5=CNC6=CC=CC=C65)C(=O)NC(CC(C)C)C(=O)NC(CC7=CNC8=CC=CC=C87)C(=O)NCCO)NC(=O)C(C)NC(=O)CNC(=O)C(C(C)C)NC=O

InChi: 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