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50845 Sigma-Aldrich

Gramicidin A from Bacillus brevis

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Properties

Related Categories A - K, Antibacterial, Antibiotics, Antibiotics A to Z, Antibiotics G-M,
Quality Level   100
biological source   Bacillus brevis
form   solid
color   white to off-white
Mode of action   cell membrane | interferes
  enzyme | inhibits
antibiotic activity spectrum   Gram-negative bacteria
  Gram-positive bacteria
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

Description

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 <REFERENCE ID="119564" TYPE="literature"/><REFERENCE ID="119563" TYPE="literature"/><REFERENCE ID="119614" TYPE="literature"/>. 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.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
MD8230000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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