Article ID Journal Published Year Pages File Type
1369848 Bioorganic & Medicinal Chemistry Letters 2016 4 Pages PDF
Abstract

Wittig reaction of methyl pyropheophorbide-d possessing the 3-formyl group gave readily methyl pyropheophorbides-a bearing a variety of 3-alkenyl groups as semi-synthetic models of chlorophyll-a. The 3-substituents rotated around the C3–C31 bond from the coplanar conformation with the chlorin π-system, moving the redmost visible absorption maxima to a shorter wavelength. The model experiments showed that natural chlorophyll-a carrying the 3-vinyl group would take a similar rotamer to control its intrinsic site energy.

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Physical Sciences and Engineering Chemistry Organic Chemistry
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