The principal investigator states that the biliproteins are a family of naturally occurring chromophores which are made up of linear tetrapyrrole derivatives covalently bonded to a protein (P) and that the most important member of this group is phytochrome (1), which functions as the """"""""on-off"""""""" switch for photomorphogenesis in higher plants. He notes that photomorphogenesis can be divided conceptually into three stages: reception of light by means of a pigment(s), transduction of the light signal from pigment to gene, and the induction of development through genetic regulation and that in comparison to photosynthesis, where some aspects of the mechanism are known in considerable detail, relatively little is known about photomorphogenesis at the molecular level. It is reported that phytochrome (1) has been implicated in such light-dependent, irreversible processes as seed germination, flowering, and stem and leaf growth; as well as reversible modulations controlling leaflet and chloroplast movement, root tip adhesion, potassium uptake, and transmembrane potentials. The principal investigator states that research in this area is important, since at present we have little knowledge of how phytochrome (1) governs the growth, development and aging of plants. He notes that in part this is due to a lack of suitable model systems, as well as the extraordinary difficulties associated with the isolation and purification of the parent chromophore. In this proposal, he outlines synthetic studies which are to alleviate these difficulties. He notes that the methodology described is highly flexible (Method C), and allows for complete control over both relative and absolute stereochemistry, as well as regiochemical control across the backbone of the tetrapyrrole skeleton. It is indicated that flexibility of this type is important not only for the syntheses of 1, but also for the preparation of related porphyrins, corrins, and other biologically important tetrapyrroles.

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
3R01GM038913-09S1
Application #
2646506
Study Section
Medicinal Chemistry Study Section (MCHA)
Project Start
1987-07-01
Project End
1998-06-30
Budget Start
1997-09-01
Budget End
1998-06-30
Support Year
9
Fiscal Year
1997
Total Cost
Indirect Cost
Name
Dartmouth College
Department
Chemistry
Type
Schools of Arts and Sciences
DUNS #
041027822
City
Hanover
State
NH
Country
United States
Zip Code
03755
Dror, Shimshon Ben; Bronshtein, Irena; Garini, Yuval et al. (2009) The localization and photosensitization of modified chlorin photosensitizers in artificial membranes. Photochem Photobiol Sci 8:354-61
Ben Dror, Shimshon; Bronshtein, Irena; Weitman, Hana et al. (2009) The binding of analogs of porphyrins and chlorins with elongated side chains to albumin. Eur Biophys J 38:847-55
Wang, Hui; Tassa, Carlos; Jacobi, Peter A (2008) Toward the synthesis of cobyric acid. Enantioselective syntheses of completely differentiated ring D synthons. Org Lett 10:2837-40
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O'Neal, William G; Roberts, William P; Ghosh, Indranath et al. (2006) Studies in chlorin chemistry. 3. A practical synthesis of c,d-ring symmetric chlorins of potential utility in photodynamic therapy. J Org Chem 71:3472-80
O'Neal, William G; Roberts, William P; Ghosh, Indranath et al. (2005) Studies in chlorin chemistry. II. A versatile synthesis of dihydrodipyrrins. J Org Chem 70:7243-51
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Jacobi, Peter A; Li, Yongkai (2003) Enantioselective syntheses of ring-C precursors of vit. B(12). Reagent control. Org Lett 5:701-4
Jacobi, Peter A; Tassa, Carlos (2003) Enantioselective syntheses of ring-C precursors of vitamin B12. Substrate control. A novel Si-assisted elimination of vinyl bromides. Org Lett 5:4879-82
Ghosh, Indranath; Jacobi, Peter A (2002) Lewis acid-promoted oxidative addition of thioimidates to Pd0. J Org Chem 67:9304-9

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