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50845

Sigma-Aldrich

Gramicidin A from Bacillus brevis

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About This Item

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

biological source

Bacillus brevis

Quality Level

100

form

solid

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

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

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

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

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

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

50845-100MG:
50845-BULK:
50845-5MG:
50845-500MG:
50845-VAR:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
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
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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