mersacidin
mersacidin Basic information
- Product Name:
- mersacidin
- Synonyms:
-
- mersacidin
- L-Isoleucinamide, L-cysteinyl-(2S,3S)-2-amino-3-mercaptobutanoyl-L-phenylalanyl-(2S,3S)-2-amino-3-mercaptobutanoyl-L-leucyl-L-prolylglycylglycylglycylglycyl-L-valyl-L-cysteinyl-(2S,3S)-2-amino-3-mercaptobutanoyl-L-leucyl-(2S,3S)-2-amino-3-mercaptobutanoyl-2,3-didehydroalanyl-L-α-glutamyl-L-cysteinyl...
- CAS:
- 128104-18-7
- MF:
- C80H120N20O21S4
- MW:
- 1826.19
- Mol File:
- 128104-18-7.mol
mersacidin Chemical Properties
- Boiling point:
- 2116.4±65.0 °C(Predicted)
- Density
- 1.39±0.1 g/cm3(Predicted)
- pka
- 4.48±0.10(Predicted)
mersacidin Usage And Synthesis
Definition
ChEBI: A type-B lantibiotic containing 3-methyllanthionine and S-(2-aminovinyl)-3-methylcysteine residues and four intra-chain thioether bridges. It is obtained from Bacillus sp. HIL Y-85,54728 and is active in vivo ag inst methicillin-resistant Staphylococcus aureus (MRSA).
Synthesis
Mersacidin is a polycyclic lantibiotic characterized by thioether-bridged rings formed by unusual amino acids like lanthionine. While naturally produced via ribosomal synthesis and post-translational modification, Solid-Phase Peptide Synthesis (SPPS) is the primary chemical route for preparing analogues. The main challenge in SPPS is the selective formation of these bridges, often addressed by either incorporating pre-formed lanthionine building blocks or inducing intramolecular Michael addition on the linear peptide. This chemical approach allows for systematic modification to create novel analogues with enhanced biological activity.