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Solution Conformation of the Antibiotic 3823A (Monensin A)-Sodium Salt

✍ Scribed by Marc J. O. Anteunis

Publisher
Wiley (John Wiley & Sons)
Year
2010
Weight
623 KB
Volume
86
Category
Article
ISSN
0037-9646

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✦ Synopsis

Abstract

Extensive double irradiation experiments allowed the almost complete unraveling and extraction of the parameters in the ^1^H‐nmr spectrum of Na^+^‐Monensin (1). From this it is concluded that the solution conformation is in its details highly similar to the crystal state of the Ag^+^ salt. Thus rings A and E are in a somewhat distorted chair, both rings B and D are in an envelope (with the flap at respectively C‐10 and C‐18) while ring C is in a ^15^~14~T(wist). An unusual high screening and consequently low rate of proton exchange was observed for some hydroxyl protons, especially in C~6~D~6~. The small couplings observed where OH‐protons are involved allow a further deeper insight in their spatial arrangement and in their participation as ligand and hydrogen bonding. Some differences with the solid state are noted here.

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