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Structure elucidation by NMR spectroscopy of saccharolidin A, a novel antiparasitic macrolide from Saccharothrix aerocolonigenes
Author(s) -
Swanson Alistair G.,
Monday Robert A.,
Perry David A.
Publication year - 1992
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260301317
Subject(s) - chemistry , heteronuclear molecule , stereochemistry , antiparasitic , two dimensional nuclear magnetic resonance spectroscopy , nuclear magnetic resonance spectroscopy , medicine , pathology
The structure of saccharolidin A, C 38 H 60 O 9 , a macrolide with antiparasitic properties isolated from Saccharothrix aerocolonigenes , was determined by two‐dimensional NMR using a fragment‐directed approach. Complete elucidation of the structure required concerted application of a range of homo‐ and heteronuclear experiments (TOCSY, ROESY, HMQC, HMBC, HMQC‐TOCSY). Saccharolidin A is related to the hygrolides but contains a number of unique features which distinguish it from previously reported members of this family. It is unsubstituted on C‐2 and contains both a 1,3‐dioxepane ring and an unsubstituted n ‐pentyl side‐chain. The relative stereochemistry within each of the three groups of contiguous chiral centres has been determined.