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Merck

50845

Gramicidin A from Bacillus brevis

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Número CAS:
11029-61-1
UNSPSC Code:
51283112
NACRES:
NA.85
PubChem Substance ID:
329757641
EC Number:
234-259-8
Beilstein/REAXYS Number:
6461131
MDL number:
MFCD00466944

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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

SMILES string

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

biological source

Bacillus brevis

color

white to off-white

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

mode of action

cell membrane | interferes, enzyme | inhibits

storage temp.

2-8°C

Quality Level

100

form

powder

Categorías relacionadas

General description

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.

Application

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.

Biochem/physiol Actions

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.

Packaging

100mg

Other Notes

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

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
0000440215
0000440215
0000360805
0000317368
0000317368

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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)
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)
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
The gramicidin A transmembrane channel: a proposed ? (L, D) helix.
Urry D W
Proceedings of the National Academy of Sciences of the USA, 68(3), 672-676 (1971)
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