The Chemistry of Tryptophan in Peptides and Proteins
The chemistry of tryptophan (1) has probably been the object of more intense investigation than that of any other amino acids. This is undoubtedly due to the particular reactivity of the indole nucleus and to the extensive chemistry developed over the yea
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Contents Acknowledgements
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I. I ntroduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 311 II. General .............................................................. I. Structure and Reactivity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2. Chemical Synthesis ................................................. 3. Biosynthesis ........................................................ 4. Aspects of Metabolism . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
312 312 314 318 320
III. Chemistry of the Modification and Cleavage of the Tryptophanyl Peptide Bond I. Chemical Oxidation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. . . . . . . .. . . . . . . . 1.1. Peracids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1.2. Ozone . . . . . .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1.3. Miscellaneous Oxidations. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2. Photooxidation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2. I. Irradiation by Ultraviolet Light . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.2. Dye-Sensitized Photooxidation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.2.1. Conversion of Tryptophan to Hexahydropyrroloindole . . . . . . . . 2.2.2. Conversion of Tryptophan to Quinazolines . . . . . . . . . . . . . . . . . . 2.2.3. Conversion of Tryptophan to Carbolines . . . . . . . . . . . . . . . . . . . . 2.3. Ionizing Radiation. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3. Brominating Agents. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3.1. N-Bromosuccinimide ............................................ 3.2. BNPS-skatole . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3.3. Tribromocresol . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
323 324 324 328 329 331 331 333 335 337 338 339 340 340 346 348
G. Cimino et al., Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products © Springer-Verlag Wien 1976
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A. FONTANA and C. TONIOLO: 4. 2-Hydroxy-5-nitrobenzyl Bromide (Koshland's Reagent) . . . . . . . . . . . . . . . . . 349 4.1. Chemistry of the Reaction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 349 4.2. Other Nitrobenzyl Reagents . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 353 5. Sulfenyl Halides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 356 5.1. General . . . . . . . . . . . .
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