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Sigma-Aldrich

Gramicidin A from Bacillus brevis

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About This Item

Número CAS:
Beilstein:
6461131
Número CE:
Número MDL:
Código UNSPSC:
51283112
ID de substância PubChem:
NACRES:
NA.85

fonte biológica

Bacillus brevis

Nível de qualidade

forma

solid

cor

white to off-white

espectro de atividade do antibiótico

Gram-negative bacteria
Gram-positive bacteria

Modo de ação

cell membrane | interferes
enzyme | inhibits

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

CC(C)C[C@@H](NC(=O)[C@H](C)NC(=O)CNC(=O)[C@@H](NC=O)C(C)C)C(=O)N[C@@H](C)C(=O)N[C@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(C)C)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](Cc3c[nH]c4ccccc34)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](Cc5c[nH]c6ccccc56)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](Cc7c[nH]c8ccccc78)C(=O)NCCO

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

chave InChI

ZWCXYZRRTRDGQE-LUPIJMBPSA-N

Categorias relacionadas

Amino Acid Sequence

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

Descrição geral

Chemical structure: peptide
Gramicidin A is a linear pentadecapeptide antibiotic produced by Bacillus brevis. The transmembrane protein contains a left-handed helix with alternating L and D residues.

Aplicação

Gramicidin A is used for studies on bacterial cell wall permeabilization and monovalent cation channel formation. Gramicidin has also been shown to inhibit transcription of T7 phage DNA, inhibit membrane-bound epidennal adenosine triphosphatase, suppress human lymphocyte blastogenesis in vitro and prolong heart allograft survival in the rat model . It has also been used to study its role in phospholipids adsorption during air-water interface.

Ações bioquímicas/fisiológicas

Gramicidin A increases the permeability of bacterial cell membranes, which allows inorganic monovalent cations to travel through unrestricted. This destroys the ion gradient between the cytoplasm and the extracellular environment . Gramicidin A acts as neutral carrier and helps in the establishment of ion flux across the lipid bilayer.
Gramicidin A is a polypeptide antibiotic that forms single ion monovalent cation channels in biological membranes.

Embalagem

100mg

Outras notas

Keep container tightly closed in a dry and well-ventilated place.Moisture sensitive. Store under inert gas. Keep in a dry place.

Pictogramas

Exclamation mark

Palavra indicadora

Warning

Frases de perigo

Declarações de precaução

Classificações de perigo

Acute Tox. 4 Oral

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves


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Effects of gramicidin-A on the adsorption of phospholipids to the air?water interface.
Biswas S C, et al.
Biochimica et Biophysica Acta - Biomembranes, 1717(1), 41-49 (2005)
T Hirano et al.
The Journal of pharmacology and experimental therapeutics, 273(1), 223-229 (1995-04-01)
Linear polypeptide antibiotic gramicidin is known to interact with the cell membrane and deregulate cation exchange. Because perturbation of cell membrane function may suppress the immune cell network, the authors investigated the effects of gramicidin on lymphocyte blastogenesis in vitro
R Fisher et al.
Proceedings of the National Academy of Sciences of the United States of America, 79(4), 1045-1048 (1982-02-01)
Gramicidin, a peptide antibiotic produced by Bacillus brevis, inhibits initiation of transcription by RNA polymerase (nucleosidetriphosphate:RNA nucleotidyltransferase, EC 2.7.7.6). We show here that the presence of gramicidin causes an increase in the rate of cleavage of the sigma subunit of
Gramicidin S: A Potent Inhibitor of Membrane-bound Epidennal Adenosine Triphosphatase from Nicotiana tabacum L. Leaves.
Kunihiro Kasamo
Plant & Cell Physiology, 23, 195-204 (1982)
Vitaliy Oliynyk et al.
Physical chemistry chemical physics : PCCP, 15(8), 2733-2740 (2013-01-17)
We report a robust and versatile membrane protein based system for selective uptake and release of ions from nanoporous particles sealed with ion-tight lipid bilayers of various compositions that is driven by the addition of ATP or a chemical potential

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