Reaction: (1) a [protein]-L-serine + a [protein]-L-cysteine = a [protein] with lanthionine crosslink + H2O (overall reaction)
(1a) a [protein]-L-serine = a [protein]-2-aminoprop-2-enoate + H2O
(1b) a [protein]-2-aminoprop-2-enoate + a [protein]-L-cysteine = a [protein] with lanthionine crosslink
(2) a [protein]-L-threonine + a [protein]-L-cysteine = a [protein] with 3-methyllanthionine crosslink + H2O (overall reaction)
(2a) a [protein]-L-threonine = a [protein]-(Z)-2-aminobutenoate + H2O
(2b) a [protein]-(Z)-2-aminobutenoate + a [protein]-L-cysteine = a [protein] with 3-methyllanthionine crosslink
Other name(s): lanthipeptide synthetase
Systematic name: [protein]-(methyl)lanthionine hydrolase
Comments: The lanthipeptides are a family of ribosomally synthesized and post-translationally modified peptides (RiPPs) that is characterized by the presence of multiple lanthionine (Lan) and 3-methyllanthionine (MeLan) crosslinks, which are formed by lanthipeptide synthases. These enzymes catalyse dehydration of Ser/Thr residues, followed by intramolecular addition of the thiol group of a Cys residue to the dehydro amino acids, which results in the formation of the thioether crosslinks of (methyl)lanthionine.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number:
References:
1. Li, B., Yu, J.P., Brunzelle, J.S., Moll, G.N., van der Donk, W.A. and Nair, S.K. Structure and mechanism of the lantibiotic cyclase involved in nisin biosynthesis. Science 311 (2006) 1464-1467. [PMID: 16527981]
2. Willey, J.M. and van der Donk, W.A. Lantibiotics: peptides of diverse structure and function. Annu. Rev. Microbiol. 61 (2007) 477-501. [PMID: 17506681]
3. Li, B. and van der Donk, W.A. Identification of essential catalytic residues of the cyclase NisC involved in the biosynthesis of nisin. J. Biol. Chem. 282 (2007) 21169-21175. [PMID: 17513866]
4. Goto, Y., Li, B., Claesen, J., Shi, Y., Bibb, M.J. and van der Donk, W.A. Discovery of unique lanthionine synthetases reveals new mechanistic and evolutionary insights. PLoS Biol. 8 (2010) e1000339. [PMID: 20351769]
5. Zhang, Q., Yu, Y., Velasquez, J.E. and van der Donk, W.A. Evolution of lanthipeptide synthetases. Proc. Natl. Acad. Sci. USA 109 (2012) 18361-18366. [PMID: 23071302]