Misplaced Pages

Gramicidin S

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.

This is an old revision of this page, as edited by Jeremiah (talk | contribs) at 20:17, 28 July 2007 (Updates and references. still chipping away.). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Revision as of 20:17, 28 July 2007 by Jeremiah (talk | contribs) (Updates and references. still chipping away.)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff) Pharmaceutical compound
Gramicidin S
Clinical data
Routes of
administration		Topical
Identifiers
IUPAC name
  • Gramicidin S
CAS Number
PubChem CID
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC60H92N12O10
Molar mass1140.7059 g/mol g·mol
File:GS.png
Crystal structure of modified Gramicidin S. Modification includes Boc groups on the ornithine as well as methylation of select amide nitrogens to force cyclic conformation.

Gramicidin S or Gramicidin Soviet is a derivative of gramicidin, produced by the Gram positive bacterium Bacillus brevis. Gramicidin S is a cyclodecapeptide, constructed as two identical pentapeptides joined head to tail, formally written as cyclo(-Val-Orn-Leu-D-Phe-Pro-)2. That is to say, it forms a ring structure composed of five different amino acids, each one used twice within the structure.Another interesting point is that it utilizes two amino acids uncommon in peptides: ornithine as well as the unnatural stereoisomer of phenylalanine. It is synthesized by gramicidin S synthetase.

Structurally, Gramicidin S differs from Gramicidin D, which is a linear peptide and forms a beta helix in cellular membranes. The exact mechanism by which Gramicidin S works is not well known.

It has a molecular mass of ca. 1,140 and is a solid, usually encapsulated in two-percent sterile spirit solution. First used in 1943 by USSR during World War II (thus is also known as Gramicidin S). It also exists in the form of pills (Latin: tabulettae Gramicidini) and paste (pasta Gramicidini). The last could be also used as a contraceptive, being introduced into vagina by the special syringe.

References

  1. "Stereochemistry of Protected Ornithine Side Chains of Gramicidin S Derivatives: X-ray Crystal Structure of the Bis-Boc-tetra-N-methyl Derivative of Gramicidin S", J. Am. Chem. Soc.; (124): 12684 - 12688;, 2002;, doi:10.1021/ja020307t {{citation}}: |first= missing |last= (help); Check date values in: |year= (help)CS1 maint: extra punctuation (link) CS1 maint: multiple names: authors list (link) CS1 maint: year (link)
  2. Gause, G. F. & Brazhnikova, M. G. (1944). Nature (London), 154, 703.
  3. Llamas-Saiz, Antonio (2007), "Double-stranded helical twisted b-sheet channels in crystals of gramicidin S grown in the presence of trifluoroacetic and hydrochloric acids", Acta Crystallographica Section D, D63: 401–407, doi:10.1107/S0907444906056435
  4. Brick, Peter (1997), "Structural basis for the activation of phenylalanine in the non-ribosomal biosynthesis of gramicidin S", The EMBO Journal, 16: 4174–4183, doi:10.1093/emboj/16.14.4174{{citation}}: CS1 maint: date and year (link)

Acta Cryst. (2007). D63, 401-407

Stub icon

This protein-related article is a stub. You can help Misplaced Pages by expanding it.

Categories: