- The preparation of all-trans uniformly 13C-labeled retinal via a modular total organic synthetic strategy. Emerging central contribution of organic synthesis toward the structure and function study with atomic resolution in protein research
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Uniformly [13C20]-labeled all-trans-retinal (1) has been prepared via a convergent modular total organic strategy with high isotope incorporation (>99%) and without isotope dilution starting from commercially available 99% enriched
- Creemers, Alain F. L.,Lugtenburg, Johan
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p. 6324 - 6334
(2007/10/03)
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- Biosynthesis of Porphyrins and Related Macrocycles. Part 35. Discovery of a Novel Dipyrrolic Cofactor Essential for the Catalytic Action of Hydroxymethylbilane Synthase (Porphobilinogen Deaminase)
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The enzyme hydroxymethylbilane synthase constructs the open-chain hydroxymethylbilane by assembly of four porphobilinogen units head-to-tail, the first of these being covalently bound to the enzyme through a group X.The surprising discovery is made that X
- Hart, Graham J.,Miller, Andrew D.,Beifuss, Uwe,Leeper, Finian J.,Battersby, Alan R.
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p. 1979 - 1993
(2007/10/02)
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- Biosynthesis of Porphyrins and Related Macrocycles. Part 16. Proof that the Single Intramolecular Rearrangement leading to Natural Porphyrins (Type-III) occurs at the Tetrapyrrole Level
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The unrearranged aminomethylbilane (2) is synthesised by a rational route and is proved to be converted by the enzymes deaminase and cosynthetase, working co-operatively, into uro'gen-III (3).The single rearrangement step established earlier is thus proved to take place at the tetrapyrrole level.Synthesis of singly 13C-labelled bilane (2) followed by its enzymic conversion into uro'gen-III serves to register each of the pyrrole rings of the product relative to the initial bilane.Finally, methods for synthesis of the bilane are developed in two different doubly 13C-labelled forms to allow the following key points to be established largely by 13C n.m.r. spectroscopy: (a) as the bilane system is converted into uro'gen-III, intramolecular rearrangement of the terminal ring D occurs, and (b) the linear tetrapyrrole is converted intact into uro'gen-III.Syntheses of -, and -uroporphyrin octamethyl ester are described together with improved h.p.l.c. conditions for the separation of isomeric coproporphyrin tetramethyl esters.
- Battersby, Alan R.,Fookes, Christopher J. R.,Meegan, Mary J.,McDonald, Edward,Wurziger, Hanns K. W.
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p. 2786 - 2799
(2007/10/02)
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