Gramicidin S

• CAT Number: I011399
• CAS Number: 113-73-5
• Molecular Formula: C60H92N12O10
• Molecular Weight: 1141.47
• Purity: ≥95%
• Synonyms: Gramicin S-A; Gramicin S 1; Gramicidin S [INN]
• Target: Bacterial
• Storage: Store at RT
• Related CAS: Gramicidin C
• IUPAC Name: (3R,6S,9S,12S,15S,21R,24S,27S,30S,33S)-9,27-bis(3-aminopropyl)-3,21-dibenzyl-6,24-bis(2-methylpropyl)-12,30-di(propan-2-yl)-1,4,7,10,13,19,22,25,28,31-decazatricyclo[31.3.0.015,19]hexatriacontane-2,5,8,11,14,20,23,26,29,32-decone
• 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
• InChIKey: IUAYMJGZBVDSGL-XNNAEKOYSA-N
• SMILES: CC(C)CC1C(=O)NC(C(=O)N2CCCC2C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N3CCCC3C(=O)NC(C(=O)NC(C(=O)N1)CCCN)C(C)C)CC4=CC=CC=C4)CC(C)C)CCCN)C(C)C)CC5=CC=CC=C5

Gramicidin S (CAT: I011399) is a cyclic decapeptide antibiotic active against both Gram-positive and Gram-negative bacteria as well as against several pathogenic fungi. However, the clinical application of GS is limited because of GS hemolytic activity. Many GS analogs with potentially attenuated hemolytic activity have been developed over the last two decades.

Reference

1: Hackl EV, Berest VP, Gatash SV. Interaction of polypeptide antibiotic gramicidin S with platelets. J Pept Sci. 2012 Dec;18(12):748-54. doi: 10.1002/psc.2461. Epub 2012 Oct 19. PubMed PMID: 23086903.