Gramicidin

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Synonyms: Gramicidin

IUPAC Name:

None

Functional Activity:

It is used primarily as a Monovalent cation ionophore.

Gramicidin is active against Gram-positive bacteria, except for the Gram-positive bacilli, and against select Gram-negative organisms, such as Neisseria bacteria. Its therapeutic use is limited to topical application as it induces hemolysis in lower concentrations than bacteria cell death, thus cannot be administered internally. The exterior epidermis is composed of dead cells, thus applying it to the surface of the skin will not cause harm.

It is also used as a topical antibiotic and is one of the three constituents of consumer antibiotic Polysporin Ophthalmic Solution.

Technical Data:

M.Wt: 1882.3

Formula: C₉₉H₁₄₀ N₂₀O₁₇

Solubility: Soluble to 100 mM in water

Storage: Dessicate at 4°C

CAS No.: 1405-97-6

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References for Gramicidin:

1. Mori, T. and Okamoto, Y. Folding simulations of gramicidin A into the beta-helix conformations: Simulated annealing molecular dynamics study. J Chem Phys, 131: 165103, 2009.

2. Majd, S., Yusko, E. C., MacBriar, A. D., Yang, J., and Mayer, M. Gramicidin pores report the activity of membrane-active enzymes. J Am Chem Soc, 131: 16119-16126, 2009.

3. Knijnenburg, A. D., Spalburg, E., de Neeling, A. J., Mars-Groenendijk, R. H., Noort, D., Grotenbreg, G. M., van der Marel, G. A., Overkleeft, H. S., and Overhand, M. Ring-extended derivatives of gramicidin S with furanoid sugar amino acids in the turn region have enhanced antimicrobial activity. ChemMedChem, 4: 1976-1979, 2009.

4. Patel, S., Davis, J. E., and Bauer, B. A. Exploring ion permeation energetics in gramicidin A using polarizable charge equilibration force fields. J Am Chem Soc, 131: 13890-13891, 2009.

5. Tamaki, M., Sasaki, I., Nakao, Y., Shindo, M., Kimura, M., and Uchida, Y. Gramicidin S analogs having six basic amino acid residues. J Antibiot (Tokyo), 62: 597-599, 2009.

6. Siu, S. W. and Bockmann, R. A. Low free energy barrier for ion permeation through double-helical gramicidin. J Phys Chem B, 113: 3195-3202, 2009.

Certificate of Analysis/MSDS is available upon request with lot number