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CAS No.: | 113-73-5 |
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Name: | GRAMICIDIN C |
Article Data: | 28 |
Cas Database | |
Molecular Structure: | |
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Formula: | C60H92 N12 O10 |
Molecular Weight: | 1141.46 |
Synonyms: | 1H,5H-Dipyrrolo[1,2-a:1',2'-p][1,4,7,10,13,16,19,22,25,28]decaazacyclotriacontine,cyclic peptide deriv.; Cyclo(L-leucyl-D-phenylalanyl-L-prolyl-L-valyl-L-ornithyl-L-leucyl-D-phenylalanyl-L-prolyl-L-valyl-L-ornithyl);Cyclo(L-valyl-L-ornithyl-L-leucyl-D-phenylalanyl-L-prolyl-L-valyl-L-ornithyl-L-leucyl-D-phenylalanyl-L-prolyl);Gramicidin C; Gramicidin C (Russian); Gramicidin S 1; Gramicidin S-A; Grammidin |
Density: | 1.24g/cm3 |
Boiling Point: | 1394.8°Cat760mmHg |
Flash Point: | 797.4°C |
Solubility: | 0.14g/L(28 oC) |
PSA: | 353.38000 |
LogP: | 4.71140 |
Cyclo[(Val-Orn-(Cbz)-Leu-DPhe-Pro)2]
Gramicidin S
Conditions | Yield |
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With hydrogen; palladium In acetic acid for 4h; | 90% |
With hydrogen; palladium on activated charcoal Hydrogenolysis; | |
With hydrogen |
D-Phe-Pro-Val-Orn-Leu-D-Phe-Pro-Val-Orn-Leu
Gramicidin S
Conditions | Yield |
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at 150℃; for 4h; Inert atmosphere; Neat (no solvent); | 87% |
[Orn(Boc)2,2']gramicidin
Gramicidin S
Conditions | Yield |
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With trifluoroacetic acid In dichloromethane for 0.5h; | 78% |
With trifluoroacetic acid In dichloromethane for 1h; | |
With chlorotriisopropylsilane; trifluoroacetic acid In water for 1.5h; | |
With trifluoroacetic acid In water at 20℃; for 1h; | 57 mg |
Gramicidin S
Conditions | Yield |
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With pyridine In N,N-dimethyl-formamide at 25℃; for 24h; | 65% |
Gramicidin S
Conditions | Yield |
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Stage #1: C70H110N12O15 With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide Stage #2: With trifluoroacetic acid | 53% |
A
Gramicidin S
Conditions | Yield |
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Stage #1: (S)-2-[(S)-5-tert-Butoxycarbonylamino-2-((S)-2-{[(S)-1-((R)-2-tert-butoxycarbonylamino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-methyl-butyrylamino)-pentanoylamino]-4-methyl-pentanoic acid 2,5-dioxo-pyrrolidin-1-yl ester With trifluoroacetic acid dealkoxycarbonylation; Stage #2: With pyridine In N,N-dimethyl-formamide at 25℃; for 24h; Dimerization; cyclization; | A 38% B 15% |
Boc-D-Phe-Pro-Val-Orn(Boc)-OH
A
Gramicidin S
Conditions | Yield |
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Stage #1: Boc-D-Phe-Pro-Val-Orn(Boc)-OH; H-Leu-oxime resin With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol Stage #2: With trifluoroacetic acid In dichloromethane for 0.5h; Stage #3: With acetic acid; N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 25℃; for 24h; | A 35% B n/a |
Conditions | Yield |
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With pyridine In N,N-dimethyl-formamide at 25℃; for 24h; Yield given. Yields of byproduct given; |
D-Phe-L-Pro
Gramicidin S
Conditions | Yield |
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Yield given. Multistep reaction; |
Gramicidin S
Conditions | Yield |
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Stage #1: TentaGel-PEG-CONH-CH2CH2S-Leu-Orn-Val-Pro-D-Phe-Leu-Orn-Val-Pro-D-Phe-NH2 With 3-(N-morpholino)propanesulfonate buffer; GrsB TE at 37℃; for 3h; pH=7.0; Enzymatic reaction; Stage #2: With trifluoroacetic acid In water |