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Merck

G5002

Gramicidin

from Bacillus aneurinolyticus (Bacillus brevis), powder or crystalline powder, antibiotic

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About This Item

CAS Number:
1405-97-6
UNSPSC Code:
12161501
NACRES:
NA.77
EC Number:
215-790-4
MDL number:
MFCD00131232

Product Name

Gramicidin from Bacillus aneurinolyticus (Bacillus brevis), Linear polypeptide antibiotic complex. A mixture of gramicidins A, B, C, and D.

SMILES string

[nH]1c2c(c(c1)C[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC=O)C(C)C)C)CC(C)C)C)C(C)C)C(C)C)C(C)C)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](Cc7c8c([nH]c7)cccc8)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](Cc5c6c([nH]c5)

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-SORVKSEFSA-N

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

mode of action

cell membrane | interferes
enzyme | inhibits

storage temp.

2-8°C

Quality Level

200

Related Categories

Application

Gramicidin from Bacillus aneurinolyticus (Bacillus brevis) has been used as a control to measure the rate of diffusion of protonated β-lactams through the lipid bilayer in liposome swelling assay. It has also been used as an analyte for the purpose of infrared laser desorption or ionization from silicon.

Biochem/physiol Actions

Linear polypeptide antibiotic mixture of gramicidin A, B, C, and D.
Linear polypeptide antibiotic mixture of gramicidin A, B, C, and D. Gramicidin A acts as neutral carrier and helps in the establishment of ion flux across the lipid bilayer.
Linear polypeptide antibiotic, a mixture of gramicidin A, B, C, and D. Gramicidin D, a channel-forming ionophore that flip-flops slowly across the membrane is a known Pgp substrate and surprisingly was found to inhibit Pgp ATPase activity. This inhibition was reversed by other Pgp substrates suggesting a common drug binding site among MDR substrate-type drugs and chemosensitizers.

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000506794
0000506794
0000413403
0000413402
0000413404

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Philipp Rühl et al.
Communications biology, 4(1), 1164-1164 (2021-10-09)
The cellular resting membrane potential (Vm) not only determines electrical responsiveness of excitable cells but also plays pivotal roles in non-excitable cells, mediating membrane transport, cell-cycle progression, and tumorigenesis. Studying these processes requires estimation of Vm, ideally over long periods
Porin channels in Escherichia coli: studies with liposomes reconstituted from purified proteins.
Nikaido H and Rosenberg E Y
Journal of Bacteriology, 153(1), 241-252 (1983)
Tatsushi Mogi et al.
Cellular and molecular life sciences : CMLS, 66(23), 3821-3826 (2009-08-25)
Gramicidin S and polymyxins are small cationic cyclic peptides and act as potent antibiotics against Gram-negative and Gram-positive bacteria by perturbing integrity of the bacterial membranes. Screening of a natural antibiotics library with bacterial membrane vesicles identified gramicidin S as
E J Prenner et al.
Biochimica et biophysica acta, 1462(1-2), 201-221 (1999-12-11)
Gramicidin S (GS) is a cyclic decapeptide of primary structure [cyclo-(Val-Orn-Leu-D-Phe-Pro)(2)] secreted by Bacillus brevis. It is a powerful antimicrobial agent with potent cidal action on a wide variety of Gram-negative and Gram-positive bacteria as well as on several pathogenic
The pore dimensions of gramicidin A.
Smart O S, et al.
Biophysical Journal, 65(6), 2455-2460 (1993)
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Product Information Sheet - G5002

Product Information Sheet

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