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J. Biol. Chem., Vol. 268, Issue 3, 1658-1669, Jan, 1993

Phycobilins of cryptophycean algae. Novel linkage of dihydrobiliverdin in a phycoerythrin 555 and a phycocyanin 645

DE Wemmer, GJ Wedemayer and AN Glazer
Department of Chemistry, Lawrence Berkeley Laboratory, University of California, Berkeley 94720.

Cryptomonad strain IVF2 phycoerythrin 555 carries phycoerythrobilins attached through single thioether bonds at alpha-Cys-18, beta-Cys-82, and beta-Cys-158 and a doubly linked 15,16-dihydrobiliverdin (DBV) at beta-DiCys-50,61 (for sequence numbering, see Sidler, W., Nutt, H., Kumpf, B., Frank, G., Suter, F., Brenzel, A., Wehrmeyer, W., and Zuber, H. (1990) Biol. Chem. Hoppe-Seyler 371, 573-547). Analysis of the beta- DiCys-50,61-linked DBV by 1H homonuclear and 1H-13C heteronuclear NMR spectroscopy establishes that the thioether bond from Cys-50 is to the 3"-carbon of the DBV ring A and that from Cys-61 is to the 18'-carbon of ring D, i.e. the peptide-linked bilin is an 8,12-bis(2-carboxyethyl)- 3-(2-(cysteinyl-S)-ethyl)-18-(1-(cysteinyl-S)-e thyl)- 2,7,13,17- tetramethylbiladiene-ab-1,19(16H,21H)-dione. DBV is also present at beta-DiCys-50,61 in cryptomonad strain UW374 phycocyanin 645 (Wedemayer, G. J., Kidd, D. G., Wemmer, D. E., and Glazer, A. N. (1992) J. Biol. Chem. 267, 7315-7331). NMR spectroscopy shows that the thioether bonds to this DBV are also at 3" and 18'. Linkage of tetrapyrroles to polypeptides through the 3"-carbon has not hitherto been reported.
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