Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Organic and Biological
Self-Assembly of Synthetic Bacteriochlorophyll-f Analogues Having C8-Formyl Group
Shin-ichi SasakiHitoshi Tamiaki
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2004 Volume 77 Issue 4 Pages 797-800

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Abstract

31-Epimerically pure C8-formyl analogues Zn–3R/S of zinc methyl bacteriopheophorbide-f (Zn–MBPhe-f) were synthesized. Their spectroscopic and self-aggregation properties were compared to those of Zn–MBPhe-f possessing the C7-formyl group (Zn–2R/S) as a model compound of bacteriochlorophyll-f. Movement of a formyl group from the 7- to 8-position as in Zn–2 → Zn–3 caused large spectral changes in both monomeric and oligomeric forms. Monomeric Zn–3R/S in THF showed a more red-shifted Qy peak (650 nm) than Zn–2R/S (628 nm), but both afforded the same Soret maximum at 448 nm. Self-aggregates of Zn–3R/S in 6% (v/v) THF–H2O gave a more red-shifted Qy peak accompanied by a large diastereomeric control in the oligomeric Qy peaks.

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© 2004 The Chemical Society of Japan
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