GRAMICIDIN C

Base Information

• Chemical Name: GRAMICIDIN C
• CAS No.: 113-73-5
• Molecular Formula: C60H92 N12 O10
• Molecular Weight: 1141.46
• Mol file: 113-73-5.mol

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

Chemical Property of GRAMICIDIN C

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 1394.8°Cat760mmHg
• PKA: 13.00±0.70(Predicted)
• Flash Point: 797.4°C
• PSA: 353.38000
• Density: 1.24g/cm³
• LogP: 4.71140
• Water Solubility.: 0.14g/L(28 oC)

Purity/Quality:

99%, ^*data from raw suppliers

GRAMICIDIN C 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Therapeutic Function: Antibacterial

Technology Process of GRAMICIDIN C

There total 33 articles about GRAMICIDIN C which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

Cyclo[(Val-Orn-(Cbz)-Leu-DPhe-Pro)2] (15207-29-1) → Gramicidin S (113-73-5)

Guidance literature:

With hydrogen; palladium; In acetic acid; for 4h;

DOI:10.1246/cl.1981.1367

Reference yield: 87.0%

D-Phe-Pro-Val-Orn-Leu-D-Phe-Pro-Val-Orn-Leu (83830-88-0) → Gramicidin S (113-73-5)

Guidance literature:

at 150 ℃; for 4h; Inert atmosphere; Neat (no solvent);

DOI:10.1021/ol102800j

Reference yield: 78.0%

[Orn(Boc)2,2']gramicidin (41839-95-6) → Gramicidin S (113-73-5)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 0.5h;

DOI:10.1021/jo0487449

upstream raw materials:

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

D-Phe-L-Pro

(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

Fmoc-Val-OH

Downstream raw materials:

C₆₄H₉₀F₆N₁₂O₁₂

C₆₆H₁₀₆N₁₂O₁₀⁽²⁺⁾*2I^(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-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)

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)

Refernces

Synthesis of gramicidin S (GS) analogs, [3-4-δAva]-GS and [3-4,3'-4'-bis(δAva)-GS (δAva=5-aminovaleric acid)

10.1246/bcsj.59.185

The research focuses on the synthesis and evaluation of Gramicidin S (GS) analogs, specifically [3Ava5-]-GS and [3Ava4,3'-]-GS, where Ava represents 5-Aminovaleric Acid. These analogs involve replacing one or two L-leucyl-p-phenylalanyl residues of GS with 5-aminovaleric acid residues. Various chemicals played crucial roles in the synthesis process. For instance, Boc-Val-Orn(Z)-OH, H-Leu-D-Phe-Pro-OMe, and Boc-Pro-OH were used as starting materials or intermediates. Reagents like DCC (dicyclohexylcarbodimide), HOBt (1-hydroxybenzotriazole), and isopentyl nitrite were employed in coupling and conversion reactions. Solvents such as THF (tetrahydrofuran), DMF (N,N-dimethylformamide), and MeOH (methanol) were utilized in different steps of the synthesis. The study also involved the use of protecting groups like Boc (t-butoxycarbonyl) and Z (benzyloxycarbonyl), and their removal was achieved using methods involving HCI (hydrochloric acid) and Pd (palladium) catalysts. The synthesized analogs were characterized and their antimicrobial activities were assessed, revealing insights into the contributions of the amide bond and side chains in the GS structure to its antimicrobial properties.

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