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:

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)

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)

C₆₆H₁₀₆N₁₂O₁₀⁽²⁺⁾*2I^(1-)

C₆₄H₉₀F₆N₁₂O₁₂

Refernces

• 1、 Sun, Haixia,Chen, Daoyuan,Zhan, Siyue,Wu, Weijian,Xu, Huiying,Luo, Chunxiang,Su, Hui,Feng, Yanqiao,Shao, Weiyan,Wan, Arabella,Zhou, Binhua,Wan, Guohui,Bu, Xianzhang. "Design and Discovery of Natural Cyclopeptide Skeleton Based Programmed Death Ligand 1 Inhibitor as Immune Modulator for Cancer Therapy". . p. 11286 - 11301. Retrieved 2020.
• 2、 Bu, Xianzhang,Wu, Xiaoming,Ng, Na Lee Joyce,Mak, Chun Kit,Qin, Chuanguang,Guo, Zhihong. "Synthesis of Gramicidin S and Its Analogues via an On-Resin Macrolactamization Assisted by a Predisposed Conformation of the Linear Precursors". . p. 2681 - 2685. Retrieved 2004.
• 3、 Tamaki, Makoto,Komiya, Seiji,Akabori, Sadatoshi,Muramatsu, Ichiro. "Relationship between the cyclization and conformation of pentapeptide active esters related to gramicidin S having no protecting group on the side chain of the ornithine residue". . p. 899 - 904. Retrieved 1997.
• 4、 Wu, Xiaoming,Bu, Xianzhang,Wong, Ka Man,Yan, Weili,Guo, Zhihong. "Biomimetic synthesis of gramicidin s and analogues by enzymatic cyclization of linear precursors on solid support.". . p. 1749 - 1752. Retrieved 2003.
• 5、 -. "Antimicrobial analogues of gramicidin S". Page/Page column 29; 33; 34. . Retrieved 2019/07/29.