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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

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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O S Andersen et al.
Indian journal of biochemistry & biophysics, 33(5), 331-342 (1996-10-01)
The linear gramicidins are peptide antibiotics that form cation-selective channels in lipid bilayers. Gramicidin channels have very well-defined functional characteristics, and the structure of membrane-spanning gramicidin A channels is known at atomic resolution. These features make the gramicidins well suited
S B Hladky
Novartis Foundation symposium, 225, 93-107 (1999-09-03)
Can we use rate constants and state models to describe ion transport through gramicidin channels? Maybe, but only if rate constants are just proportionality constants between rates and probabilities of observing states of the channel. This approach is natural if
N Akaike
Nihon yakurigaku zasshi. Folia pharmacologica Japonica, 113(6), 339-347 (1999-10-19)
Cl- is one of the major ionic constituents of cells and extracellular spaces. Intracellular Cl- plays an important role in regulating the cell volume and pH, in both salt secretion and reabsorption, in membrane excitability, and G-protein-dependent intracellular signal transduction.
[Structural and functional characteristics of gramicidin S in connection with its antibiotic activity].
A N Polin et al.
Antibiotiki i khimioterapiia = Antibiotics and chemoterapy [sic], 48(12), 29-32 (2004-06-05)
Devaki A Kelkar et al.
Biochimica et biophysica acta, 1768(9), 2011-2025 (2007-06-19)
The linear peptide gramicidin forms prototypical ion channels specific for monovalent cations and has been extensively used to study the organization, dynamics and function of membrane-spanning channels. In recent times, the availability of crystal structures of complex ion channels has
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