Gramicidin S

Gramicidin S
Clinical data
Routes of; administration	Topical
Identifiers
	IUPAC name Gramicidin S;
CAS Number	113-73-5 ;
PubChem CID	73357;
ChemSpider	66085 ;
UNII	WHM29QA23F;
ChEBI	CHEBI:5530 ;
ChEMBL	ChEMBL373496 ;
NIAID ChemDB	002002;
CompTox Dashboard (EPA)	DTXSID6046008 ;
Chemical and physical data
Formula	C60H92N12O10
Molar mass	1141.470 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)C[C@H]1C(=O)N[C@@H](C(=O)N2CCC[C@H]2C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N3CCC[C@H]3C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CCCN)C(C)C)Cc4ccccc4)CC(C)C)CCCN)C(C)C)Cc5ccccc5;
	InChI InChI=1S/C60H92N12O10/c1-35(2)31-43-53(75)67-45(33-39-19-11-9-12-20-39)59(81)71-29-17-25-47(71)55(77)70-50(38(7)8)58(80)64-42(24-16-28-62)52(74)66-44(32-36(3)4)54(76)68-46(34-40-21-13-10-14-22-40)60(82)72-30-18-26-48(72)56(78)69-49(37(5)6)57(79)63-41(23-15-27-61)51(73)65-43/h9-14,19-22,35-38,41-50H,15-18,23-34,61-62H2,1-8H3,(H,63,79)(H,64,80)(H,65,73)(H,66,74)(H,67,75)(H,68,76)(H,69,78)(H,70,77)/t41-,42-,43-,44-,45+,46+,47-,48-,49-,50-/m0/s1 ; Key:IUAYMJGZBVDSGL-XNNAEKOYSA-N ;
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Gramicidin S or Gramicidin Soviet^[1] is an antibiotic that is effective against some gram-positive and gram-negative bacteria as well as some fungi.

It is a derivative of gramicidin, produced by the gram-positive bacterium Brevibacillus 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.^[2] Another interesting point is that it utilizes two amino acids uncommon in peptides: ornithine as well as the atypical stereoisomer of phenylalanine. It is synthesized by gramicidin S synthetase.^[3]

^ Gause GF, Brazhnikova MG (1944). "Gramicidin S and its use in the Treatment of Infected Wounds". Nature. 154 (3918): 703. Bibcode:1944Natur.154..703G. doi:10.1038/154703a0. S2CID 4125407.
^ Llamas-Saiz AL, Grotenbreg GM, Overhand M, van Raaij MJ (March 2007). "Double-stranded helical twisted beta-sheet channels in crystals of gramicidin S grown in the presence of trifluoroacetic and hydrochloric acids". Acta Crystallographica. Section D, Biological Crystallography. 63 (Pt 3): 401–7. Bibcode:2007AcCrD..63..401L. doi:10.1107/S0907444906056435. PMID 17327677.
^ Conti E, Stachelhaus T, Marahiel MA, Brick P (July 1997). "Structural basis for the activation of phenylalanine in the non-ribosomal biosynthesis of gramicidin S". The EMBO Journal. 16 (14): 4174–83. doi:10.1093/emboj/16.14.4174. PMC 1170043. PMID 9250661.

[1] Gause GF, Brazhnikova MG (1944). "Gramicidin S and its use in the Treatment of Infected Wounds". Nature. 154 (3918): 703. Bibcode:1944Natur.154..703G. doi:10.1038/154703a0. S2CID 4125407.

[2] Llamas-Saiz AL, Grotenbreg GM, Overhand M, van Raaij MJ (March 2007). "Double-stranded helical twisted beta-sheet channels in crystals of gramicidin S grown in the presence of trifluoroacetic and hydrochloric acids". Acta Crystallographica. Section D, Biological Crystallography. 63 (Pt 3): 401–7. Bibcode:2007AcCrD..63..401L. doi:10.1107/S0907444906056435. PMID 17327677.

[3] Conti E, Stachelhaus T, Marahiel MA, Brick P (July 1997). "Structural basis for the activation of phenylalanine in the non-ribosomal biosynthesis of gramicidin S". The EMBO Journal. 16 (14): 4174–83. doi:10.1093/emboj/16.14.4174. PMC 1170043. PMID 9250661.

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Clinical data


Routes of administration	Topical
Identifiers
IUPAC name Gramicidin S
CAS Number	113-73-5^Y
PubChem CID	73357
ChemSpider	66085^Y
UNII	WHM29QA23F
ChEBI	CHEBI:5530^Y
ChEMBL	ChEMBL373496^Y
NIAID ChemDB	002002
CompTox Dashboard (EPA)	DTXSID6046008
Chemical and physical data
Formula	C₆₀H₉₂N₁₂O₁₀
Molar mass	1141.470 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(C)C[C@H]1C(=O)N[C@@H](C(=O)N2CCC[C@H]2C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N3CCC[C@H]3C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CCCN)C(C)C)Cc4ccccc4)CC(C)C)CCCN)C(C)C)Cc5ccccc5
InChI InChI=1S/C60H92N12O10/c1-35(2)31-43-53(75)67-45(33-39-19-11-9-12-20-39)59(81)71-29-17-25-47(71)55(77)70-50(38(7)8)58(80)64-42(24-16-28-62)52(74)66-44(32-36(3)4)54(76)68-46(34-40-21-13-10-14-22-40)60(82)72-30-18-26-48(72)56(78)69-49(37(5)6)57(79)63-41(23-15-27-61)51(73)65-43/h9-14,19-22,35-38,41-50H,15-18,23-34,61-62H2,1-8H3,(H,63,79)(H,64,80)(H,65,73)(H,66,74)(H,67,75)(H,68,76)(H,69,78)(H,70,77)/t41-,42-,43-,44-,45+,46+,47-,48-,49-,50-/m0/s1^Y Key:IUAYMJGZBVDSGL-XNNAEKOYSA-N^Y
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