Gramicidin S
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Grundinformationen
- CAS
113-73-5- Standard-SMILES
CC(C)C[C@@H]1NC(=O)[C@H](CCCN)NC(=O)[C@H](C(C)C)NC(=O)[C@@H]2CCCN2C(=O)[C@@H](Cc2ccccc2)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN)NC(=O)[C@H](C(C)C)NC(=O)[C@@H]2CCCN2C(=O)[C@@H](Cc2ccccc2)NC1=O- InChIKey
IUAYMJGZBVDSGL-XNNAEKOYSA-N- Summenformel
- C60H92N12O10
- Durchschnittliche Molmasse
- 1.141,47 g/mol
- Monoisotopische Masse
- 1.140,70593714
Namen und Bezeichner
- Bevorzugter Name
- Gramicidin S
- IUPAC
- Cyclo(L-leucyl-D-phenylalanyl-L-prolyl-L-valyl-L-ornithyl-L-leucyl-D-phenylalanyl-L-prolyl-L-valyl-L-ornithyl)
- Englischer Name
- GRAMICIDIN C
- Summenformel
- C60H92N12O10
- Molmasse
- 1141.45
Namen und Synonyme
GRAMICIDIN SGramicidin S-AGRAMICIDIN CGramicidin S1Soviet Gramicidin CGramicidin S TFA saltGramicidin S (8CI, 9CI, ACI)Cyclo(L-Val-L-Orn-L-Leu-D-Phe-L-Pro-L-Val-L-Orn-L-Leu-D-Phe-L-Pro-)Cyclo(L-Leu-D-Phe-L-Pro-L-Val-L-Orn-L-Leu-D-Phe-L-Pro-L-Val-L-Orn-)HCO-X-GLY-L-ALA-D-LEU-L-ALA-D-VAL-L-VAL-D-VAL-L-TRP-D-LEU-L-PHE-D-LEU-L-TRP-D-LEU-L-TRP-NHCH2CH2OH
Datenbank-Bezeichner
- CAS
113-73-5- PubChem CID
- 73357
- DTXSID
DTXSID6046008- ChEMBL
CHEMBL373496- ChEBI
CHEBI:5530- UNII
- WHM29QA23F
- Nikkaji
- J10.597J
Eigenschaften
Physikochemische Eigenschaften
- Schmelzpunkt
- 265 · 265-270 °C (decomp)(Solv: ethanol (64-17-5); ethyl ether (60-29-7))
- Siedepunkt
- 827.42 °C · 827.42°C (rough estimate)
- Dichte
- 1.0265 · 1.0265 (rough estimate)
- Brechungsindex
- 1.6 · 1.6000 (estimate)
- pka
- 13 · 13.00±0.70(Predicted)
- Aggregatzustand
- Solid
- Farbe
- White to off-white
- Wasserlöslichkeit
- 0.14 g/L · 0.14g/L(28 ºC)
- InChIKey
- IUAYMJGZBVDSGL-XNNAEKOYSA-N
Chemie und Industrie
Anwendungen
BeschreibungGramicidin S was found in the culture broth of Bacillus brevis by Gause of the USSR Academy of Medical Sciences in 1944. It was later found by Otani of Osaka University in the cells of the Nagano strain of the same species. The antibiotic is a basic peptide showing strong activity against gram-positive bacteria and considerable activity against gramnegative cocci and Mycobacterium. Gramicidin S is rather toxic but is not absorbed orally; it is used topically as an ointment or as eye or ear drops in combination with other antibacterial drugs.
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Ergänzende Hinweise
DefinitionA cyclic peptide that acts on gram-positive bacteria.
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