Organic Chemistry

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By F.P. Schmidtchen

Many organic structures nonetheless carry numerous very fascinating molecular homes that to date can't be matched by way of manmade analogs. studying concerning the rules and methods utilized by nature may supply entry to novel nanostructures, more suitable catalysts for the functionalization of hydrocarbon compounds or may possibly permit catalytic C-C bond formation below environmentally benign stipulations. This quantity recapitulates the cutting-edge in these sectors of bioorganic chemistry that, instead of mimick the typical instance, goal to make use of the underlying ideas for worthy purposes.

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Gibb BC, Mezo AR, Sherman JC (1995) Tetrahedron Lett 36:7587 40. (a) Lieberman M, Sasaki T (t991) J Am Chem Soc 113: 1470, (b) ibid (1993) Tetrahedron 49: 3677; (c) Lieberman M, Tabet M, Sasaki T (1994) J Am Chem Soc 116:5053 41. Ghadiri MR, Soares C, Choi C (1992) J Am Chem Soc 114:825 42. Ghadiri MR, Case MA (1993) Angew Chem Int Ed Engl 32:1594 43. Ghadiri MR, Soares C, Choi C (1992) J Am Chem Soc 114:4000 36 The Development of Peptide Nanostructure 44. 45. 46. 47. Minoura N (1993) J Chem Soc Chem Commun 1993:196 Berthet M, Yordanov S, Sonveaux E (1986) Makromol Chem Rapid Commun 7:205 Berthet M, Sonveaux E (1986) Biopolymers 25:189 (a) Anzai J, Ueno A, Osa T (1982) Makromol Chem Rapid Commun 3: 55; (b) Anzai J, Ueno A, Osa T (1980) Makromol Chem Rapid Commun 1:741 48.

2 H y d r o x y l a t i o n s of N o n a c t i v a t e d C - H B o n d s . . . . . . 3 Allylic H y d r o x y l a t i o n s . . . . . . . . . . . . 4 E p o x i d a t i o n s . . . . . . . . . . . . . . . 5 Benzylic H y d r o x y l a t i o n s . . . . . . . . . . . . 6 A r o m a t i c H y d r o x y l a t i o n s . . . . . . . . . . . 7 O x i d a t i o n s I n v o l v i n g H e t e r o a t o m P a r t i c i p a t i o n . . . . .

These other rate factors usually lead to much smaller (masked) observed isotope effects. Accordingly the observed kn/ko is fully expressed in the P450 catalyzed hydroxylation of 24. Both studies provide important clues concerning the transition state geometry, because the observation of a fully expressed primary isotope effect indicates a rate determining H" removal by the oxo-iron intermediate 13,--~14 in a highly symmetrical fashion. Furthermore, the observation of overall retention of configuration suggests a very fast trapping of the intermediate alkyl radical by the hydroxylated iron(IV)porphyrin in the "cage" of the active site.

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