TY - JOUR
T1 - Legonaridin, a new member of linaridin RiPP from a Ghanaian Streptomyces Isolate
AU - Rateb, Mostafa
AU - Zhai, Yin
AU - Ehrner, Emmanuelle
AU - Rath, Christopher M.
AU - Wang, Xiaoling
AU - Tabudravu, Jioji
AU - Ebel, Rainer
AU - Bibb, Mervin
AU - Kyeremeh, Kwaku
AU - Dorrestein, Pieter C.
AU - Hong, Kui
AU - Jaspars, Marcel
AU - Deng, Hai
PY - 2015/10/7
Y1 - 2015/10/7
N2 - Linaridins are rare linear ribosomally-synthesized and post-translationally modified peptides (RiPPs) and only two, cypemycin and SGR-1832, in this family have been identified so far. Legonaridin 1 has been discovered as a new member of linaridins through chemical isolation, peptidogenomics, comprehensive 1- and 2-D NMR and advanced Marfey's analyses from the soil bacterium Streptomyces sp. CT34, an isolate collected from Legon, Ghana. Bioinformatics analysis of the gene cluster suggested that the biosynthesis of legonaridin 1 is different from those of cypemycin and SGR-1832. Consistent with bioinformatics and peptidogenomics analyses, 1 has a total of nine post-modifications, 8 dehydrobutyrine residues and a N,N-dimethylated N-terminus with a carboxylic acid at the C-terminus. Legonaridin 1 is structurally different from the two known linaridins comprising a new subfamily. This is the first time that NMR spectroscopy is used to establish the 2-D structure of a linaridin RiPP.
AB - Linaridins are rare linear ribosomally-synthesized and post-translationally modified peptides (RiPPs) and only two, cypemycin and SGR-1832, in this family have been identified so far. Legonaridin 1 has been discovered as a new member of linaridins through chemical isolation, peptidogenomics, comprehensive 1- and 2-D NMR and advanced Marfey's analyses from the soil bacterium Streptomyces sp. CT34, an isolate collected from Legon, Ghana. Bioinformatics analysis of the gene cluster suggested that the biosynthesis of legonaridin 1 is different from those of cypemycin and SGR-1832. Consistent with bioinformatics and peptidogenomics analyses, 1 has a total of nine post-modifications, 8 dehydrobutyrine residues and a N,N-dimethylated N-terminus with a carboxylic acid at the C-terminus. Legonaridin 1 is structurally different from the two known linaridins comprising a new subfamily. This is the first time that NMR spectroscopy is used to establish the 2-D structure of a linaridin RiPP.
UR - http://www.rsc.org/suppdata/c5/ob/c5ob01269d/c5ob01269d1.pdf
U2 - 10.1039/C5OB01269D
DO - 10.1039/C5OB01269D
M3 - Article
SN - 1477-0539
SP - 9585
EP - 9592
JO - Organic & Biomolecular Chemistry
JF - Organic & Biomolecular Chemistry
IS - 37
ER -
