Diastereoisomers of an ‘arsenomethionine’-based structure from Sargassum lacerifolium : the formation of the arsenic–carbon bond in arsenic-containing natural products

Author:

Edmonds John S

Publisher

Elsevier BV

Subject

Organic Chemistry,Clinical Biochemistry,Drug Discovery,Pharmaceutical Science,Molecular Biology,Molecular Medicine,Biochemistry

Reference15 articles.

1. Francesconi, K. A.; Edmonds, J. S.; Stick, R. V.; Skelton, B. W.; White, A. H. J. Chem. Soc., Perkin Trans. 1, 1991, 2707.

2. Speciation of arsenic by reversed-phase high performance liquid chromatography-inductively coupled plasma mass spectrometry.

3. 1H NMR spectra (500 MHz, D2O) Fast diastereoisomer (eluting first from ODS column). δ 1.92, 1.96, 2s, Me2As+; 2.59, dd, J1″,1″ 13.7 Hz, J1″,2″ 4.4 Hz, H1″; 2.64, dd, J5,5 14.3 Hz, J4,5 10.2 Hz, H5; 2.70, dd, J1″,1″ 13.7 Hz, J1″,2″ 10.9 Hz, H1″; 2.82, dd, J5,5 14.3 Hz, J4,5 2.8 Hz, H5; 2.93, m, H2″; 3.49, dd, J4″,4″ 10.9Hz, J4″,5″ 6.5Hz, H4″; 3.53, dd, J6″,6″ 11.8 Hz, J5″,6″ 6.2 Hz, H6″; 3.57–363, m, H1′, 4″, 6″; 3.74, m, H3″, 3″; 3.80, dd, J1′,1′ 10.8Hz, J1′,2′ 4.3 Hz, H1′; 3.87, m, H5″; 4.01–409, m, H2′, 3′, 3′; 4.12, d, J2,3 3.9 Hz, H2; 4.19.25, m, H3, 4; 5.00, s, H1. Slow diastereoisomer. δ 1.91, 1.96, 2s, Me2As+; 2.55, dd, J1″,1″ 13.7 Hz, J1″,2″ 4.2 Hz, H1″; 2.63, dd, J5,5 14.0 Hz, J4,5 11.0 Hz, H5; 2.72, dd, J1″,1″ 13.7 Hz, J1″,2″ 11.1 Hz, H1″; 2.81, dd, J5,5 14.0 Hz, J4,5 2.2 Hz, H5; 2.92, m, H2″; 3.50, dd, J4″,4″ 10.6 Hz, J4″,5″ 6.7 Hz, H4″; 3.54, dd, J6″,6″ 11.6 Hz, J5″,6″ 6.3 Hz, H6″; 3.57, dd, J4″,4″ 10.6 Hz, J4″,5″ 3.9 Hz, H4″; 3.60, dd, J6″,6″ 11.6 Hz, J5″6″ 3.5 Hz, H6″; 3.62, dd, J1′,1′ 10.6 Hz, J1′,2′ 4.4 Hz, H1′; 3.72, dd, J3″,3″ 9.8 Hz, J2″,3″ 4.5 Hz, H3″; 3.77, dd, J3″,3″ 9.8 Hz, J2″,3″ 5.8 Hz, H3″; 3.80, dd, J1′,1′ 10.6 Hz, J1′,2′ 4.5 Hz, H1′; 3.87, m, H5″; 4.01.09, m, H2′, 3′, 3′; 4.12, d, J2,3 3.9Hz, H2; 4.19.25, m, H3, 4; 5.00, s, H1.

4. Arsenic compounds from marine organisms

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