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Impact of peripheral substituents in regioselective synthesis of position-10 or position-20 bromo-bacteriochlorins
- Title
- Impact of peripheral substituents in regioselective synthesis of position-10 or position-20 bromo-bacteriochlorins
- Authors
- Dukh, Mykhaylo; Joshi, Penny; Ohkubo, Kei; Tabaczynski, Walter; Patel, Nayan J.; Missert, Joseph R.; Zador, Steve; Fukuzumi, Shunichi; Pandey, Ravindra K.
- Ewha Authors
- Shunichi Fukuzumi
- SCOPUS Author ID
- Shunichi Fukuzumi
- Issue Date
- 2017
- Journal Title
- TETRAHEDRON LETTERS
- ISSN
- 0040-4039
- Citation
- TETRAHEDRON LETTERS vol. 58, no. 9, pp. 851 - 854
- Keywords
- Chlorin; Bacteriochlorin; Bovine serum albumin; Density functional calculations
- Publisher
- PERGAMON-ELSEVIER SCIENCE LTD
- Indexed
- SCIE; SCOPUS
- Document Type
- Article
- Abstract
- Bacteriochlorins derived either from chlorophyll-a or bacteriochlorophyll-a on reacting with pyridinium bromide or N-bromosuccinimide (NBS) gave the corresponding 10- or 20-bromo analogues. In contrast to methyl bacteriopyropheophorbide-a, which afforded 10-bromo derivative, the 7-keto and 8-ketobacterichlorins under similar reaction conditions gave the corresponding 20-bromo analogues exclusively. In both series, the nature of substituents present at position-3 did not make any difference in the reaction outcome. Density functional calculations were carried out to clarify the difference in reactions outcome. Density functional calculations were carried out to clarify the difference in reactivity of bromination at 10- and 20- mesa positions. (C)2017 Elsevier Ltd. All rights reserved.
- DOI
- 10.1016/j.tetlet.2017.01.044
- Appears in Collections:
- 자연과학대학 > 화학·나노과학전공 > Journal papers
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