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Merck

G0550000

Gramicidin

European Pharmacopoeia (EP) Reference Standard

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About This Item

CAS Number:
1405-97-6
MDL number:
MFCD00131232
UNSPSC Code:
41116107
NACRES:
NA.24

Key Documents

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Product Name

Gramicidin, European Pharmacopoeia (EP) Reference Standard

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

grade

pharmaceutical primary standard

API family

gramicidin

manufacturer/tradename

EDQM

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

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Application

This European Pharmacopoeia reference standard is intended for use only as specifically prescribed in the European Pharmacopoeia.

General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.
For further information and support please go to the website of the issuing Pharmacopoeia.

Other Notes

Sales restrictions may apply.

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

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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
Gramicidin perforated patch recording and intracellular chloride activity in excitable cells.
N Akaike
Progress in biophysics and molecular biology, 65(3), 251-264 (1996-01-01)
Olaf S Andersen et al.
IEEE transactions on nanobioscience, 4(1), 10-20 (2005-04-09)
Gramicidin channels are mini-proteins composed of two tryptophan-rich subunits. The conducting channels are formed by the transbilayer dimerization of nonconducting subunits, which are tied to the bilayer/solution interface through hydrogen bonds between the indole NH groups and the phospholipid backbone
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
Trial by ordeal: ionic free energies in gramicidin.
Peter C Jordan
Biophysical journal, 83(3), 1235-1236 (2002-08-31)
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