Nisin

Base Information

• Chemical Name: Nisin
• CAS No.: 1414-45-5
• Molecular Formula: C143H230N42O37S7
• Molecular Weight: 3354.25
• Mol file: 1414-45-5.mol

Synonyms:1-Thia-4,7,10,13,16,19-hexaazacyclodocosane, cyclic peptide deriv.;1H,9H-Pyrrolo[2,1-i][1,4,7,10]thiatriazacyclotridecine, cyclic peptide deriv.;9,19-Dithia-2,5,13,16,22-pentaazabicyclo[9.9.2]docosane, cyclic peptide deriv.;Ambicin N;Delvoplus;MicroGARD MG 300;Nisaplin;Nisin(1-34);Nisitrol;Novasin;NisinA (9CI);

Chemical Property of Nisin

Chemical Property:

• Appearance/Colour: grey or white or light yellow powder
• Refractive Index: 1.635
• Boiling Point: 2966.771 °C at 760 mmHg
• Flash Point: 1748.039 °C
• PSA: 1390.67000
• Density: 1.402 g/cm³
• LogP: 3.42180
• Storage Temp.: 2-8°C
• Solubility.: insoluble in H2O; insoluble in EtOH; ≥5.63 mg/mL in DMSO with gentle warming and ultrasonic
• Water Solubility.: Soluble in water

Purity/Quality:

99% ^*data from raw suppliers

Nisin ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• General Description: Nisin is a peptide antibiotic characterized by its complex structure, which includes cyclic sulfide peptides and dehydroalanine residues. The synthesis of its ring A component, a key structural feature, has been achieved through innovative methods such as desulfurization of cyclic disulfide peptides and Hofmann degradation of 2,3-diaminopropionyl residues. These approaches effectively address the challenges of incorporating dehydroamino acids and forming sulfide rings, as confirmed by analytical techniques like NMR and mass spectrometry. Nisin's structural complexity underscores its significance as a natural antimicrobial agent.

Refernces

Synthetic study on peptide antibiotic nisin. I. The synthesis of ring A

10.1246/bcsj.56.2044

This study focuses on the synthesis of ring A, a cyclic sulide peptide part containing dehydroalanine residues, in the peptide antibiotic nisin. The researchers employed two novel procedures: first, they derived a sulfide ring from a cyclic disulfide peptide through desulfurization with tris(diethylamino)phosphine (P(Et3N)3); second, they developed a simple and convenient method for preparing dehydroalanyl residues via Hofmann degradation of 2,3-diaminopropionyl residues in the presence of a sulfide linkage. The study successfully synthesized ring A, addressing challenges such as the introduction of dehydroamino acid residues and the formation of the sulfide ring. The synthesized ring A was confirmed through various analytical techniques, including NMR, FD-MS, and amino acid analysis, demonstrating the effectiveness of the new methods in synthesizing complex natural products like nisin.