title: Solid-state NMR analysis of calcium and d-mannose binding of BMY-28864, a water-soluble analogue of pradimicin A.
abstract: Pradimicin A (PRM-A) is a unique antibiotic with a lectin-like ability to recognize d-mannopyranosides (Man) in the presence of Ca(2+) ion. BMY-28864 (1) is a water-soluble analogue of PRM-A, which has been extensively used for studies on the mode of Man recognition and antifungal action of pradimicins. Although it has been assumed that PRM-A and 1 bind Man in a similar fashion, direct experimental evidence has yet to be provided. In this report, we compared Ca(2+) and Man binding of 1 with that of PRM-A through two solid-state NMR experiments. The solid-state (113)Cd NMR analysis using (113)Cd(2+) ion as a surrogate for Ca(2+) ion suggested the similarity in Ca(2+) coordination of PRM-A and 1. The dipolar assisted rotational resonance (DARR) analysis using (13)C-labeled 1 clearly showed that 1 as well as PRM-A binds Man near its carboxyl group. These results collectively indicate that the mode of binding of Ca(2+) ion and Man is nearly identical between PRM-A and 1.
authors.affiliation: Synthetic Cellular Chemistry Laboratory, RIKEN Advanced Science Institute, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan. yu@riken.jp
authors.forename: Yu
authors.initials: Y
authors.lastname: Nakagawa
authors.forename: Takashi
authors.initials: T
authors.lastname: Doi
authors.forename: K
authors.initials: K
authors.lastname: Takegoshi
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Igarashi
authors.forename: Yukishige
authors.initials: Y
authors.lastname: Ito
mesh_terms: D018943:Anthracyclines / Q000737:chemistry*; D001665:Binding Sites; D002118:Calcium / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000592:standards; D008358:Mannose / Q000737:chemistry*; D008968:Molecular Conformation; D012015:Reference Standards; D012995:Solubility; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry
chemical_list: D018943:Anthracyclines; D014867:Water; C067714:N,N-dimethylpradimicin FA-2; D008358:Mannose; D002118:Calcium