Gramicidin A from Bacillus brevis

Name: Gramicidin A from <I>Bacillus brevis</I>
Brand: SIGMA

Slide 1 of 1

Select a Size

Pricing and availability is not currently available.

About This Item

CAS Number:

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

Key Documents

View All Documentation

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

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

Quality Level

100

Related Categories

Antibiotics

Biochemicals

Cell Culture Supplements & Reagents

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item	G5002	50847	368020
Sigma-Aldrich 50845 Gramicidin A from Bacillus brevis	Sigma-Aldrich G5002 Gramicidin from Bacillus aneurinolyticus (Bacillus brevis)	Sigma-Aldrich 50847 Gramicidin C from Bacillus brevis	Sigma-Aldrich 368020 Gramicidin A, High Purity, Bacillus brevis
antibiotic activity spectrum Gram-negative bacteria, Gram-positive bacteria	antibiotic activity spectrum Gram-negative bacteria, Gram-positive bacteria	antibiotic activity spectrum Gram-negative bacteria, Gram-positive bacteria	antibiotic activity spectrum -
mode of action cell membrane \| interferes, enzyme \| inhibits	mode of action cell membrane \| interferes, enzyme \| inhibits	mode of action cell membrane \| interferes, enzyme \| inhibits	mode of action -
Quality Level 100	Quality Level 200	Quality Level 100	Quality Level 100
form solid	form -	form powder	form solid
storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C	storage temp. −20°C
biological source Bacillus brevis	biological source -	biological source Bacillus brevis	biological source -

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 [1] [2] [3]. It has also been used to study its role in phospholipids adsorption during air-water interface.[4]

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 [5]. Gramicidin A acts as neutral carrier and helps in the establishment of ion flux across the lipid bilayer.[6]

Gramicidin A is a polypeptide antibiotic that forms single ion monovalent cation channels in biological membranes.

General description

Chemical structure: peptide

Gramicidin A is a linear pentadecapeptide antibiotic produced by Bacillus brevis.[7] The transmembrane protein contains a left-handed helix with alternating L and D residues.[6]

Other Notes

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

Packaging

100mg

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

ppe

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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 as a potential immunosuppressant for organ transplantation: suppression of human lymphocyte blastogenesis in vitro and prolongation of heart allograft survival in the rat.

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

An interaction between gramicidin and the sigma subunit of RNA polymerase.

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)

Selective and ATP-driven transport of ions across supported membranes into nanoporous carriers using gramicidin A and ATP synthase.

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

View All Related Papers

Questions

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service