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Remarkable regioselective position-10 bromination of bacteriopyropheophorbide-a and ring-B reduced pyropheophorbide-a.


ABSTRACT: Both bacteriopyropheophorbide-a and ring-B reduced pyropheophorbide-a on reacting with NBS (N-bromosuccinamide) undergo electrophilic bromination to provide 10-bromo analogs. The electronic nature of the substituents present at position-3 did not make any difference in the regioselective outcome of the brominated products. These relatively stable brominated chlorins and bacteriochlorins provide an easy way of introducing a wide variety of functionalities, which could be extremely useful in developing improved agents for biomedical applications and supramolecular chemistry.

SUBMITTER: Ethirajan M 

PROVIDER: S-EPMC3076286 | biostudies-literature | 2011 Apr

REPOSITORIES: biostudies-literature

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Remarkable regioselective position-10 bromination of bacteriopyropheophorbide-a and ring-B reduced pyropheophorbide-a.

Ethirajan Manivannan M   Joshi Penny P   William White H WH   Ohkubo Kei K   Fukuzumi Shunichi S   Pandey Ravindra K RK  

Organic letters 20110321 8


Both bacteriopyropheophorbide-a and ring-B reduced pyropheophorbide-a on reacting with NBS (N-bromosuccinamide) undergo electrophilic bromination to provide 10-bromo analogs. The electronic nature of the substituents present at position-3 did not make any difference in the regioselective outcome of the brominated products. These relatively stable brominated chlorins and bacteriochlorins provide an easy way of introducing a wide variety of functionalities, which could be extremely useful in devel  ...[more]

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