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Sigma-Aldrich

Gramicidin A

from Bacillus brevis, ≥90% (HPLC), solid, ion channel-forming pentadecapeptide, Calbiochem®

Synonym(s):

Gramicidin A, High Purity, Bacillus brevis, gA

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About This Item

Empirical Formula (Hill Notation):
C99H140N20O17
CAS Number:
11029-61-1
Molecular Weight:
1882.29
MDL number:
MFCD00466944
UNSPSC Code:
51283112
NACRES:
NA.77

product name

Gramicidin A, High Purity, Bacillus brevis, Gramicidin A, High Purity, Bacillus brevis, CAS 11029-61-1, is a naturally-occurring ion channel-forming pentadecapeptide. Causes K+/H+ exchange in mitochondria in a non-voltage dependent manner.

Quality Level

100

Assay

≥90% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze

impurities

<5% gC isomers (HPLC)

color

white to off-white

solubility

DMSO: 100 mg/mL

shipped in

ambient

storage temp.

−20°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-LUPIJMBPSA-N

General description

Naturally occurring, ion channel-forming pentadecapeptide antibiotic that renders membranes permeable to protons and alkali metal ions. Causes red blood cell lysis at concentrations of 0.5-1.0 µg/ml. Gramicidin A causes K+/H+ exchange in mitochondria in a non-voltage dependent manner.
Naturally-occurring ion channel-forming pentadecapeptide. The association of two gA peptides causes the formation of a monovalent cation-selective ion channel. Causes K+/H+ exchange in mitochondria in a non-voltage dependent manner. Causes red blood cell lysis at 0.5-1.0 µg/ml.

Biochem/physiol Actions

Cell permeable: no
Primary Target
Causes the formation of a monovalent cation-selective ion channel
Product does not compete with ATP.
Reversible: no

Warning

Toxicity: Harmful (C)

Sequence

HCO-Val-Gly-Ala-D-Leu-Ala-D-Val-Val-D-Val-Trp-D-Leu-Trp-D-Leu-Trp-D-Leu-Trp-NHCH₂CH₂OH

Reconstitution

Following recosntituion, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

Quigley, E.P., et al. 2000. J. Membr. Biol. 174,207.
Koeppe, R.E., et al. 1995. Biochemistry34, 9299.
Ketchem, R.R., et al. 1993. Science261, 1457.
Stankovic, C.J., et al. 1990. Anal. Biochem.184, 100.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

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

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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