Gramicidin C

Base Information

• Chemical Name: Gramicidin C
• CAS No.: 1405-97-6
• Molecular Formula: C99H140N20O17
• Molecular Weight: 1882.32
• Hs Code.: 2941906000
• NSC Number: 757043
• Mol file: 1405-97-6.mol

Synonyms:Gramicidin;Gramicidin A;Gramicidin A(1);Gramicidin B;Gramicidin C;Gramicidin D;Gramicidin Dubos;Gramicidin J;Gramicidin K;Gramicidin NF;Gramicidin P;Gramicidin S;Gramicidin, Linear;Gramicidins;Gramoderm;Linear Gramicidin

Chemical Property of Gramicidin C

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 229-230℃
• Refractive Index: 1.595
• Boiling Point: 1394.8°C at 760 mmHg
• Flash Point: 797.4°C
• PSA: 548.99000
• Density: 1.24g/cm³
• LogP: 11.26260
• Storage Temp.: 2-8°C
• Solubility.: Practically insoluble in water, soluble in methanol, sparingly soluble in alcohol
• Water Solubility.: Soluble in acetic acid and lower alcohols. Practically insoluble in water.
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 16
• Exact Mass: 1140.70593718
• Heavy Atom Count: 82
• Complexity: 2020

Purity/Quality:

98%,99%, ^*data from raw suppliers

Gramicidin(TechnicalGrade) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21-36/37/38
• Safety Statements: 26-36-24/25-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CC1C(=O)NC(C(=O)N2CCCC2C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N3CCCC3C(=O)NC(C(=O)NC(C(=O)N1)CCCN)C(C)C)CC4=CC=CC=C4)CC(C)C)CCCN)C(C)C)CC5=CC=CC=C5
• Description: Gramicidin is a polypeptide antibiotic mixture of gramicidin A , gramicidin B, and gramicidin C originally isolated from B. brevis. It is also a component of the antibiotic tyrothricin . Gramicidin is active against the Gram-positive bacterium S. aureus but not Gram-negative E. coli. It also protects mice from Pneumococcus infection in vivo when administered at a dose of 0.002 mg/animal. Gramicidin inhibits growth of bacteria by forming pores and channels in the cell wall, which increases its permeability to monovalent cations. Formulations containing gramicidin have been used as topical agents in the treatment of bacterial skin infections.
• Uses: Medicine (antibacterial). Gramicidins are a family of linear pentadecapeptides isolated from Bacillus brevis by Dubos at the Rockefeller Institute in 1939. Gramicidin is a complex of six closely related analogues A1, A2, B1, B2, C1 and C2 where A1 and A2 are the dominant components. Gramidicins act by forming channels in cell membranes causing ion leakage, and is an essential bioprobe for understanding the nature of the cell membranes. Targets primarily the cell membrane of Gram-positive bacteria and shows little effect against Gram-negative bacteria. Gramicidin is typically used as a topical antimicrobial agent because it also causes hemolysis of red blood cells.
• Clinical Use: The use of gramicidin is restricted to topical applications on wounds or as ear and eye drops. Currently, much research is being invested to generate less toxic analogs that still exhibit the same wide range of bactericidal activity. To date, no new gramicidin-like polypeptides are available for clinical use. Gramicidin is used in some countries as a topical contraceptive, because it has spermostatic activity.

Technology Process of Gramicidin C

There total 2 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:

C117H166N19O24Pol + ethanolamine (141-43-5) → Gramicidin A (1405-97-6)

Guidance literature:

C₁₁₇H₁₆₆N₁₉O₂₄Pol; With trifluoroacetic acid; In water; at 20 ℃; hydroxymethylbenzoic acid-TentaGel macrobeads

ethanolamine; In N,N-dimethyl-formamide; at 50 ℃; hydroxymethylbenzoic acid-TentaGel macrobeads

DOI:10.1038/s41467-020-18711-2

Reference yield:

C119H172N20O25 → Gramicidin A (1405-97-6)

Guidance literature:

With chlorotriisopropylsilane; water; trifluoroacetic acid; phenol; In dichloromethane; at 25 ℃; for 1h; Inert atmosphere;

DOI:10.1021/bi100857g

upstream raw materials:

ethanolamine

Refernces

• 1、 Hamamoto, Hiroshi,Inoue, Masayuki,Itoh, Hiroaki,Panthee, Suresh,Paudel, Atmika,Sekimizu, Kazuhisa,Takada, Yuri. "Discovery of gramicidin A analogues with altered activities by multidimensional screening of a one-bead-one-compound library". . . Retrieved 2020.