Open AccessCovalent structure of mutacin 1140 and a novel method for the rapid identification of lantibiotics
Author(s) -
Smith Leif,
Novák Jan,
Rocca Jim,
McClung Scott,
Hillman J. D.,
Edison Arthur S.
Publication year - 2000
Publication title -
european journal of biochemistry
Language(s) - English
Resource type - Journals
eISSN - 1432-1033
pISSN - 0014-2956
DOI - 10.1046/j.1432-1033.2000.01777.x
Subject(s) - lantibiotics , covalent bond , chemistry , mass spectrometry , nuclear magnetic resonance spectroscopy , chromatography , stereochemistry , organic chemistry , bacteriocin , antimicrobial
The primary structure of the Streptococcus mutans lantibiotic mutacin 1140 was elucidated by NMR spectroscopy, mass spectrometry, and chemical sequencing. The structure is in agreement with other closely related lantibiotics, such as epidermin. A novel method was developed in which mutacin 1140 was chemically modified with sodium borohydride followed by ethanethiol, allowing the differentiation of the thioether‐containing residues from the dehydrated residues. This double‐labeling strategy provides a simple method to reliably identify all modified lantibiotic residues with a minimal amount of material. While NMR spectroscopy is still required to obtain thioether bridging patterns and thus the complete covalent structure, the double‐labeling technique, along with mass spectrometry, provides most of the information in a fraction of the time required for a complete NMR analysis. Thus, with these new techniques lantibiotics can be rapidly characterized.