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113-73-5 Gramicidin S
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113-73-5 Usage

Manufacturing Process

5 lb of acid precipitated solid (Hotchkiss, Advances in Enzymology, pages 157- 158) from 30 gal of tyrothricin fermentation liquor containing about 40 g (2%)of tyrothricin were extracted with 12 liters of absolute ethyl alcohol and filtered. The filtrate was evaporated in vacuo to 1 liter, and the concentrate extracted twice with 1 liter of pentane. The pentane layers were discarded.40 g of decolorizing charcoal were added to the pentane-extracted filtrate and filtered off. To 500 ml of the charcoal-treated filtrate were added 200 ml benzene and 300 ml water, the whole shaken thoroughly, centrifuged, and the benzene layer separated. This treatment of the charcoal-treated filtrate was repeated twice, all benzene fractions were combined and evaporated in vacuo. 200 ml of absolute acetone were added to the residue and concentrated by boiling to 150 ml. The concentrate was refrigerated overnight. The crystals which had formed in the concentrate were filtered off, and the mother liquor concentrated first to 50 ml and then to 25 ml, the two concentrates refrigerated overnight, and the formed crystals filtered off. Total yield of crystalline gramicidin was 3.85 g = 19.2% of estimated tyrothricin in the initial material. The combined crystal crops were redissolved in 50 ml absolute acetone, and the solution refrigerated overnight. After filtering, the formed crystals were dried in vacuo. The total yield of crystalline gramicidin thus obtained was 2.5 g.

Purification Methods

Gramicidin S crystallises from EtOH. The di-HCl crystallises from EtOH (+ few drops of HCl) with m 277-278o (see below). [NMR: Gibbons et al. Nature 227 840 1970, Beilstein 26 III/IV 4273.]

Therapeutic Function

Antibacterial

Definition

A cyclic peptide that acts on gram-positive bacteria.

Originator

Gramoderm,Schering,US,1949
InChI:InChI=1/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

113-73-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name gramicidin S

1.2 Other means of identification

Product number -
Other names Gramicin S-A

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:113-73-5 SDS

113-73-5Synthetic route

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

Cyclo[(Val-Orn-(Cbz)-Leu-DPhe-Pro)2]

Gramicidin S
113-73-5

Gramicidin S

Conditions
ConditionsYield
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
83830-88-0

D-Phe-Pro-Val-Orn-Leu-D-Phe-Pro-Val-Orn-Leu

Gramicidin S
113-73-5

Gramicidin S

Conditions
ConditionsYield
at 150℃; for 4h; Inert atmosphere; Neat (no solvent);87%
[Orn(Boc)2,2']gramicidin
41839-95-6

[Orn(Boc)2,2']gramicidin

Gramicidin S
113-73-5

Gramicidin S

Conditions
ConditionsYield
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

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

Gramicidin S
113-73-5

Gramicidin S

Conditions
ConditionsYield
With pyridine In N,N-dimethyl-formamide at 25℃; for 24h;65%
C70H110N12O15

C70H110N12O15

Gramicidin S
113-73-5

Gramicidin S

Conditions
ConditionsYield
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

(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

Gramicidin S
113-73-5

Gramicidin S

B

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

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

Conditions
ConditionsYield
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
917501-50-9

Boc-D-Phe-Pro-Val-Orn(Boc)-OH

H-Leu-oxime resin

H-Leu-oxime resin

A

Gramicidin S
113-73-5

Gramicidin S

B

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

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

Conditions
ConditionsYield
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
H-D-Phe-Pro-Val-Orn-Leu-ONSu*TFA

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

A

Gramicidin S
113-73-5

Gramicidin S

B

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

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

Conditions
ConditionsYield
With pyridine In N,N-dimethyl-formamide at 25℃; for 24h; Yield given. Yields of byproduct given;
D-Phe-L-Pro
51926-52-4

D-Phe-L-Pro

Fmoc-protected immobolized peptide

Fmoc-protected immobolized peptide

Gramicidin S
113-73-5

Gramicidin S

Conditions
ConditionsYield
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

Gramicidin S
113-73-5

Gramicidin S

Conditions
ConditionsYield
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
(S)-2-[(S)-5-Amino-2-((S)-2-{[(S)-1-((R)-2-amino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-methyl-butyrylamino)-pentanoylamino]-4-methyl-pentanoic acid 2,5-dioxo-pyrrolidin-1-yl ester
151812-96-3

(S)-2-[(S)-5-Amino-2-((S)-2-{[(S)-1-((R)-2-amino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-methyl-butyrylamino)-pentanoylamino]-4-methyl-pentanoic acid 2,5-dioxo-pyrrolidin-1-yl ester

Gramicidin S
113-73-5

Gramicidin S

Conditions
ConditionsYield
With pyridine In N,N-dimethyl-formamide at 25℃; for 24h;
Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Boc-D-Phe-OH
18942-49-9

Boc-D-Phe-OH

Fmoc-Pro-OH
71989-31-6

Fmoc-Pro-OH

Fmoc-Orn(Boc)-OH
109425-55-0

Fmoc-Orn(Boc)-OH

Fmoc-Leu-D-Phe-Pro-Val-Orn(Boc)-Leu-(4-sulfamylbutyryl AM resin)

Fmoc-Leu-D-Phe-Pro-Val-Orn(Boc)-Leu-(4-sulfamylbutyryl AM resin)

Gramicidin S
113-73-5

Gramicidin S

Conditions
ConditionsYield
Multistep reaction;
Boc-D-Phe-Pro-Val-Orn(Boc)-Leu-D-Phe-Pro-Val-Orn(Boc)-OH

Boc-D-Phe-Pro-Val-Orn(Boc)-Leu-D-Phe-Pro-Val-Orn(Boc)-OH

H-Leu-oxime resin

H-Leu-oxime resin

A

Gramicidin S
113-73-5

Gramicidin S

B

C60H92N12O10

C60H92N12O10

Conditions
ConditionsYield
Stage #1: Boc-D-Phe-Pro-Val-Orn(Boc)-Leu-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 56 % Chromat.
B 15 % Chromat.
H-Val-Orn(Z)-OBzl

H-Val-Orn(Z)-OBzl

Gramicidin S
113-73-5

Gramicidin S

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: HOBt; EDCI / CH2Cl2 / 3 h / 0 - 20 °C
2.1: HCl / dioxane / 0.5 h / 20 °C
3.1: 3.21 g / HOBt; EDCI / CH2Cl2 / 3 h / 0 - 20 °C
4.1: hydrogen / Pd/C / methanol / 15 h
5.1: 1.90 g / NaOH / methanol; dioxane; H2O / 15 h / 20 °C
6.1: BOP; HOBt
6.2: trifluoroacetic acid / CH2Cl2 / 0.5 h
6.3: 35 percent / iPr2NEt; acetic acid / dioxane / 24 h / 25 °C
View Scheme
Boc-Val-Orn(Z)-OBzl

Boc-Val-Orn(Z)-OBzl

Gramicidin S
113-73-5

Gramicidin S

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: HCl / dioxane / 0.5 h / 20 °C
2.1: HOBt; EDCI / CH2Cl2 / 3 h / 0 - 20 °C
3.1: HCl / dioxane / 0.5 h / 20 °C
4.1: 3.21 g / HOBt; EDCI / CH2Cl2 / 3 h / 0 - 20 °C
5.1: hydrogen / Pd/C / methanol / 15 h
6.1: 1.90 g / NaOH / methanol; dioxane; H2O / 15 h / 20 °C
7.1: BOP; HOBt
7.2: trifluoroacetic acid / CH2Cl2 / 0.5 h
7.3: 35 percent / iPr2NEt; acetic acid / dioxane / 24 h / 25 °C
View Scheme
H-Pro-Val-Orn(Z)-OBzl

H-Pro-Val-Orn(Z)-OBzl

Gramicidin S
113-73-5

Gramicidin S

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 3.21 g / HOBt; EDCI / CH2Cl2 / 3 h / 0 - 20 °C
2.1: hydrogen / Pd/C / methanol / 15 h
3.1: 1.90 g / NaOH / methanol; dioxane; H2O / 15 h / 20 °C
4.1: BOP; HOBt
4.2: trifluoroacetic acid / CH2Cl2 / 0.5 h
4.3: 35 percent / iPr2NEt; acetic acid / dioxane / 24 h / 25 °C
View Scheme
Boc-D-Phe-Pro-Val-Orn-OH

Boc-D-Phe-Pro-Val-Orn-OH

Gramicidin S
113-73-5

Gramicidin S

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 1.90 g / NaOH / methanol; dioxane; H2O / 15 h / 20 °C
2.1: BOP; HOBt
2.2: trifluoroacetic acid / CH2Cl2 / 0.5 h
2.3: 35 percent / iPr2NEt; acetic acid / dioxane / 24 h / 25 °C
View Scheme
Boc-Pro-Val-Orn(Z)-OBzl

Boc-Pro-Val-Orn(Z)-OBzl

Gramicidin S
113-73-5

Gramicidin S

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: HCl / dioxane / 0.5 h / 20 °C
2.1: 3.21 g / HOBt; EDCI / CH2Cl2 / 3 h / 0 - 20 °C
3.1: hydrogen / Pd/C / methanol / 15 h
4.1: 1.90 g / NaOH / methanol; dioxane; H2O / 15 h / 20 °C
5.1: BOP; HOBt
5.2: trifluoroacetic acid / CH2Cl2 / 0.5 h
5.3: 35 percent / iPr2NEt; acetic acid / dioxane / 24 h / 25 °C
View Scheme
Boc-D-Phe-Pro-Val-Orn(Z)-OBzl
917501-48-5

Boc-D-Phe-Pro-Val-Orn(Z)-OBzl

Gramicidin S
113-73-5

Gramicidin S

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogen / Pd/C / methanol / 15 h
2.1: 1.90 g / NaOH / methanol; dioxane; H2O / 15 h / 20 °C
3.1: BOP; HOBt
3.2: trifluoroacetic acid / CH2Cl2 / 0.5 h
3.3: 35 percent / iPr2NEt; acetic acid / dioxane / 24 h / 25 °C
View Scheme
t-Boc-L-valine
13734-41-3

t-Boc-L-valine

Boc-Gly

Boc-Gly

Gramicidin S
113-73-5

Gramicidin S

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: HOBt; EDCI / CH2Cl2 / 3 h / 0 - 20 °C
2.1: HCl / dioxane / 0.5 h / 20 °C
3.1: HOBt; EDCI / CH2Cl2 / 3 h / 0 - 20 °C
4.1: HCl / dioxane / 0.5 h / 20 °C
5.1: 3.21 g / HOBt; EDCI / CH2Cl2 / 3 h / 0 - 20 °C
6.1: hydrogen / Pd/C / methanol / 15 h
7.1: 1.90 g / NaOH / methanol; dioxane; H2O / 15 h / 20 °C
8.1: BOP; HOBt
8.2: trifluoroacetic acid / CH2Cl2 / 0.5 h
8.3: 35 percent / iPr2NEt; acetic acid / dioxane / 24 h / 25 °C
View Scheme
H-Orn(Z)-OBzl
73995-50-3

H-Orn(Z)-OBzl

Gramicidin S
113-73-5

Gramicidin S

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: HOBt; EDCI / CH2Cl2 / 3 h / 0 - 20 °C
2.1: HCl / dioxane / 0.5 h / 20 °C
3.1: HOBt; EDCI / CH2Cl2 / 3 h / 0 - 20 °C
4.1: HCl / dioxane / 0.5 h / 20 °C
5.1: 3.21 g / HOBt; EDCI / CH2Cl2 / 3 h / 0 - 20 °C
6.1: hydrogen / Pd/C / methanol / 15 h
7.1: 1.90 g / NaOH / methanol; dioxane; H2O / 15 h / 20 °C
8.1: BOP; HOBt
8.2: trifluoroacetic acid / CH2Cl2 / 0.5 h
8.3: 35 percent / iPr2NEt; acetic acid / dioxane / 24 h / 25 °C
View Scheme
C70H110N12O15
1054661-52-7

C70H110N12O15

Gramicidin S
113-73-5

Gramicidin S

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.19 g / N-hydroxybenzotriazole hydrate; diisopropylethylamine; PyBOP / dimethylformamide / 16 h
2: 78 percent / CF3CO2H / CH2Cl2 / 0.5 h
View Scheme
cyclo(Val-Orn(For)-Leu-D-Phe-Pro)2

cyclo(Val-Orn(For)-Leu-D-Phe-Pro)2

Gramicidin S
113-73-5

Gramicidin S

Conditions
ConditionsYield
With hydrogenchloride In methanol at 37℃; for 21h;
C45H61N7O8S

C45H61N7O8S

A

Gramicidin S
113-73-5

Gramicidin S

B

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: water; 3,3-dimethyldioxirane / acetone / 0.17 h / 23 °C
2: water; oxalic acid / N,N-dimethyl-formamide / 48 h / 40 °C
View Scheme
C36H47N5O8

C36H47N5O8

A

Gramicidin S
113-73-5

Gramicidin S

B

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

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

Conditions
ConditionsYield
With water; oxalic acid In N,N-dimethyl-formamide at 40℃; for 48h;
C68H98N12O13
1387574-96-0

C68H98N12O13

Gramicidin S
113-73-5

Gramicidin S

Conditions
ConditionsYield
With water; oxalic acid In N,N-dimethyl-formamide at 40℃; for 48h;3.6 mg
1-(tert-butoxycarbonyl)-L-proline
15761-39-4

1-(tert-butoxycarbonyl)-L-proline

t-Boc-L-valine
13734-41-3

t-Boc-L-valine

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

(R)-5-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)pentanoic acid
2480-93-5, 16937-92-1

(R)-5-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)pentanoic acid

Boc-D-Phe-OH
18942-49-9

Boc-D-Phe-OH

Gramicidin S
113-73-5

Gramicidin S

Conditions
ConditionsYield
Stage #1: N-tert-butoxycarbonyl-L-leucine With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide
Stage #2: With trifluoroacetic acid In dichloromethane
Stage #3: 1-(tert-butoxycarbonyl)-L-proline; t-Boc-L-valine; (R)-Nδ-benzyloxycarbonyl-Nα-(tert-butoxycarbonyl)-ornithine; Boc-D-Phe-OH Further stages;
C75H114N15O12PolS

C75H114N15O12PolS

Gramicidin S
113-73-5

Gramicidin S

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 6h; aminomethyl resin;55 mg
Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

Fmoc-Leu-OH
35661-60-0

Fmoc-Leu-OH

Fmoc-D-Phe-OH
86123-10-6

Fmoc-D-Phe-OH

(R)-Pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester
71989-31-6, 109425-54-9, 144829-96-9, 101555-62-8

(R)-Pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester

Fmoc-Lys(pg)-OH

Fmoc-Lys(pg)-OH

Gramicidin S
113-73-5

Gramicidin S

Conditions
ConditionsYield
Stage #1: Fmoc-D-Phe-OH With benzotriazol-1-ol; 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 dichloromethane; N,N-dimethyl-formamide for 1.5h;
Stage #2: With piperidine In N,N-dimethyl-formamide for 0.166667h;
Stage #3: Fmoc-Val-OH; Fmoc-Leu-OH; (R)-Pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester; Fmoc-Lys(pg)-OH Further stages;
ethyl trifluoroacetate,
383-63-1

ethyl trifluoroacetate,

Gramicidin S
113-73-5

Gramicidin S

C64H90F6N12O12
86194-28-7

C64H90F6N12O12

Conditions
ConditionsYield
With triethylamine In methanol Ambient temperature;83%
Gramicidin S
113-73-5

Gramicidin S

methyl iodide
74-88-4

methyl iodide

C66H106N12O10(2+)*2I(1-)
99437-06-6

C66H106N12O10(2+)*2I(1-)

Conditions
ConditionsYield
With potassium hydrogencarbonate In methanol for 45h; Ambient temperature;75%
With potassium hydrogencarbonate In methanol Ambient temperature;75%
2,5-dioxopyrrolidin-(meta-diphenylphosphino)benzoate
1422391-48-7

2,5-dioxopyrrolidin-(meta-diphenylphosphino)benzoate

Gramicidin S
113-73-5

Gramicidin S

N,N'-(3,3'-((6R,9S,12S,15S,17aS,23R,26S,29S,32S,34aS)-6,23-dibenzyl-9,26-diisobutyl-15,32-diisopropyl-5,8,11,14,17,22,25,28,31,34-decaoxotetratriacontahydrodipyrrolo[1,2-a:1',2'-p] [1,4,7,10,13,16,19,22,25,28]decaazacyclotriacontine-12,29-diyl)bis(propane-3,1-diyl))bis(3-(diphenylphosphino)benzamide)
1422391-49-8

N,N'-(3,3'-((6R,9S,12S,15S,17aS,23R,26S,29S,32S,34aS)-6,23-dibenzyl-9,26-diisobutyl-15,32-diisopropyl-5,8,11,14,17,22,25,28,31,34-decaoxotetratriacontahydrodipyrrolo[1,2-a:1',2'-p] [1,4,7,10,13,16,19,22,25,28]decaazacyclotriacontine-12,29-diyl)bis(propane-3,1-diyl))bis(3-(diphenylphosphino)benzamide)

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h; Inert atmosphere;48%
2,5-dioxopyrrolidin-(para-diphenylphosphino)benzoate

2,5-dioxopyrrolidin-(para-diphenylphosphino)benzoate

Gramicidin S
113-73-5

Gramicidin S

N,N'-(3,3'-((6R,9S,12S,15S,17aS,23R,26S,29S,32S,34aS)-6,23-dibenzyl-9,26-diisobutyl-15,32-diisopropyl-5,8,11,14,17,22,25,28,31,34 decaoxotetratriacontahydro dipyrrolo[1,2-a:1',2'-p] [1,4,7,10,13,16,19,22,25,28] decaazacyclotriacontine-12,29-diyl)bis(propane-3,1-diyl))bis(4-(diphenylphosphino)benzamide)
1422391-50-1

N,N'-(3,3'-((6R,9S,12S,15S,17aS,23R,26S,29S,32S,34aS)-6,23-dibenzyl-9,26-diisobutyl-15,32-diisopropyl-5,8,11,14,17,22,25,28,31,34 decaoxotetratriacontahydro dipyrrolo[1,2-a:1',2'-p] [1,4,7,10,13,16,19,22,25,28] decaazacyclotriacontine-12,29-diyl)bis(propane-3,1-diyl))bis(4-(diphenylphosphino)benzamide)

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h; Inert atmosphere;48%
Gramicidin S
113-73-5

Gramicidin S

2,5-dioxopyrrolidin-1-yl 2-(diphenylphosphanyl)benzoate
291286-47-0

2,5-dioxopyrrolidin-1-yl 2-(diphenylphosphanyl)benzoate

N,N'-(3,3'-((6R,9S,12S,15S,17aS,23R,26S,29S,32S,34aS)-6,23-dibenzyl-9,26-diisobutyl-15,32-diisopropyl-5,8,11,14,17,22,25,28,31,34-decaoxotetratriacontahydrodipyrrolo[1,2-a:1',2'-p][1,4,7,10,13,16,19,22,25,28]decaazacyclotriacontine-12,29-diyl)bis(propane-3,1-diyl))bis(2-(diphenylphosphino)benzamide)
1422391-47-6

N,N'-(3,3'-((6R,9S,12S,15S,17aS,23R,26S,29S,32S,34aS)-6,23-dibenzyl-9,26-diisobutyl-15,32-diisopropyl-5,8,11,14,17,22,25,28,31,34-decaoxotetratriacontahydrodipyrrolo[1,2-a:1',2'-p][1,4,7,10,13,16,19,22,25,28]decaazacyclotriacontine-12,29-diyl)bis(propane-3,1-diyl))bis(2-(diphenylphosphino)benzamide)

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h;39%
Gramicidin S
113-73-5

Gramicidin S

3-(diphenylphosphaneyl)propanoic acid N-hydroxysuccinimide ether

3-(diphenylphosphaneyl)propanoic acid N-hydroxysuccinimide ether

(6R,9S,12S,15S,17aS,23R,26S,29S,32S,34aS)-6,23-dibenzyl-12,29-bis(3-(3-(diphenylphosphino)propanoyloxyamino)propyl)-9,26-diisobutyl-15,32-diisopropyltetracosahydrodipyrrolo [1,2-a:1',2'-p] [1,4,7,10,13,16,19,22,25,28] decaaza cyclotriacontine-5,8,11,14,17,22,25,28,31,34-decaone

(6R,9S,12S,15S,17aS,23R,26S,29S,32S,34aS)-6,23-dibenzyl-12,29-bis(3-(3-(diphenylphosphino)propanoyloxyamino)propyl)-9,26-diisobutyl-15,32-diisopropyltetracosahydrodipyrrolo [1,2-a:1',2'-p] [1,4,7,10,13,16,19,22,25,28] decaaza cyclotriacontine-5,8,11,14,17,22,25,28,31,34-decaone

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h; Inert atmosphere;16.8%
5-(4-carboxyphenyl)-10,15,20-tris(4-methylphenyl) porphyrin
61449-63-6

5-(4-carboxyphenyl)-10,15,20-tris(4-methylphenyl) porphyrin

Gramicidin S
113-73-5

Gramicidin S

C156H160N20O12

C156H160N20O12

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; benzotriazol-1-ol Acylation;

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