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G5002

Sigma-Aldrich

Gramicidin

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

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About This Item

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

product name

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

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

cell membrane | interferes
enzyme | inhibits

storage temp.

2-8°C

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

Related Categories

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 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. 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.

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

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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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)
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
T A Cross
Methods in enzymology, 289, 672-696 (1997-01-01)
The method of using orientational constraints derived from solid-state NMR for structural characterization of polypeptides in heterogeneous environments has now been demonstrated. A very high resolution structure has been achieved that has led to greater functional understanding of this channel.
The pore dimensions of gramicidin A.
Smart O S, et al.
Biophysical Journal, 65(6), 2455-2460 (1993)
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
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