Synthesis of [18,19,21,22-(13)C4]-labeled tautomycin as an NMR probe of protein phosphatase inhibitor.
We have accomplished the synthesis of 13C-labeled tautomycin at the C18, C19, C21, and C22 positions starting from 100% [13C]triethylphosphonoacetate for the purpose of elucidating the dynamics and conformation of the C17-C26 moiety. NMR spectroscopy of 13C-labeled tautomycin revealed strong binding with protein phosphatase type 1 and new features in the 13C NMR spectrum, such as the very small three-bond coupling constants (2J).
Isobe
Minoru
M
Laboratory of Organic Chemistry, Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan. isobem@agr.nagoya-u.ac.jp
Kurono
Masakuni
M
Tsuboi
Katsunori
K
Takai
Akira
A
D002247:Carbon Isotopes; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D007553:Isotope Labeling; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D010749:Phosphoprotein Phosphatases / Q000037:antagonists & inhibitors*; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D002247:Carbon Isotopes; D004791:Enzyme Inhibitors; D011714:Pyrans; D013141:Spiro Compounds; C053079:tautomycin; D010749:Phosphoprotein Phosphatases