Elucidation of salicylate attachment in celesticetin biosynthesis opens the door to create a library of more efficient hybrid lincosamide antibiotics† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c6sc04235j Click here for additional data file.

Lincomycin (863 units per mg), acetylsalicylic (13, >98%), 3-aminobenzoic (15, 98%), 4-amino-2chlorobenzoic (22, 97%), 4-amino-2-hydroxybenzoic (26, 99%), benzoic (6, >97%), 2-chlorobenzoic (8, 98%), trans-cinnamic (44, 99%), 4-coumaric (43, 98%), 2,3-dichlorobenzoic (40, 97%), 2,5-dichlorobenzoic (36, 97%), 3,4-dichlorobenzoic (31, 99%), 3,4-dihydroxybenzoic (30, 97%), 3,4-dimethoxybenzoic (32, 99%), 2,4-dinitrobenzoic (29, 96%), 3-hydroxybenzoic (14, 99%), 4-hydroxybenzoic (17, 99%), 3,4,5-trihydroxybenzoic (38, gallic, 99%), 2-methylbenzoic (7, 95%), 4-methylbenzoic (19, 98%), 2-hydroxybenzoic (4, salicylic, >97%), 4-hydroxy-3,5-dimethoxybenzoic (39, syringic, >95%) acids were obtained from Sigma-Aldrich (Germany); 4-aminobenzoic (18, 99%), 2-bromobenzoic (9, >98%), 3,5-dichlorobenzoic (34, >98%), 2,4-dihydroxybenzoic (25, >95%), 2,5-dihydroxybenzoic (35, >98%), 3,5-dihydroxybenzoic (33, >90%), 2-iodobenzoic (10, 95%), and 4-nitrobenzoic (21, >95%) acids were obtained from Fluka; 3-chlorobenzoic (16, >98%), 4-chlorobenzoic (20, >98%), 2,4-dichlorobenzoic (28, 98%), 2,6-dichlorobenzoic (24, >98%), 2,6-dihydroxybenzoic (23, >97%) acids were obtained from Merck-Schuchardt (Germany); 2-aminobenzoic (5, anthranilic, 99%), 2-hydroxy-3,5-dinitrobenzoic (42, >97%), phthalic (12, >95%), and 2-hydroxy-5-sulfobenzoic (37, p.a.) acids were obtained from Lachema (Czech Republic); 2,3-dimethoxybenzoic acid (41, >97%) was obtained from Loba-Chemie (Austria), 2-methoxybenzoic (11) and 4-(dimethylamino)benzoic acids (22) were obtained from Assoc. Prof. Jindrich Jindrich, Faculty of Sciences, Charles University in Prague. Adenosine 5 ́-triphosphate (ATP, >99%), S-adenosylmethionine (SAM, 80%), ammonium hydroxide (28-30% solution), coenzyme A disodium salt (CoA, >96%), β-nicotinamide adenine dinucleotide phosphate reduced (NADPH, 96%), pyridoxal-5 ́phosphate (PLP, >98%) were obtained from Sigma-Aldrich (Germany), formic acid (98-100%) from Merck (Germany), acetonitrile and methanol (both LC-MS grade) from Biosolve (Netherlands).