Name: GRAMICIDIN C
SKU: 113-73-5

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Basic Information

Molecular Structure:
CAS No.:	113-73-5
Name:	GRAMICIDIN C

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

Synthetic route

: 15207-29-1
Cyclo[(Val-Orn-(Cbz)-Leu-DPhe-Pro)2]

: 113-73-5
Gramicidin S

Conditions

Conditions	Yield
With hydrogen; palladium In acetic acid for 4h;	90%
With hydrogen; palladium on activated charcoal Hydrogenolysis;
With hydrogen

: 83830-88-0
D-Phe-Pro-Val-Orn-Leu-D-Phe-Pro-Val-Orn-Leu

: 113-73-5
Gramicidin S

Conditions

Conditions	Yield
at 150℃; for 4h; Inert atmosphere; Neat (no solvent);	87%

: 41839-95-6
[Orn(Boc)2,2']gramicidin

: 113-73-5
Gramicidin S

Conditions

Conditions	Yield
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

: H-(D-Phe-Pro-Val-Orn-Leu)2-ONSu

: 113-73-5
Gramicidin S

Conditions

Conditions	Yield
With pyridine In N,N-dimethyl-formamide at 25℃; for 24h;	65%

: C70H110N12O15

: 113-73-5
Gramicidin S

Conditions

Conditions	Yield
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%

: (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

A: 113-73-5
Gramicidin S

B: cyclo(D-Phe-Pro-Val-Orn-Leu)

Conditions

Conditions	Yield
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%

: 917501-50-9
Boc-D-Phe-Pro-Val-Orn(Boc)-OH

H-Leu-oxime resin: H-Leu-oxime resin

A: 113-73-5
Gramicidin S

B: cyclo(D-Phe-Pro-Val-Orn-Leu)

Conditions

Conditions	Yield
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

...Expand

: H-D-Phe-Pro-Val-Orn-Leu-ONSu*TFA

A: 113-73-5
Gramicidin S

B: cyclo(D-Phe-Pro-Val-Orn-Leu)

Conditions

Conditions	Yield
With pyridine In N,N-dimethyl-formamide at 25℃; for 24h; Yield given. Yields of byproduct given;

: 51926-52-4
D-Phe-L-Pro

Fmoc-protected immobolized peptide: Fmoc-protected immobolized peptide

: 113-73-5
Gramicidin S

Conditions

Conditions	Yield
Yield given. Multistep reaction;

TentaGel-PEG-CONH-CH2CH2S-Leu-Orn-Val-Pro-D-Phe-Leu-Orn-Val-Pro-D-Phe-NH2: TentaGel-PEG-CONH-CH2CH2S-Leu-Orn-Val-Pro-D-Phe-Leu-Orn-Val-Pro-D-Phe-NH2

: 113-73-5
Gramicidin S

Conditions

Conditions	Yield
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

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