ISSN:
1075-2617
Keywords:
histidine side chains
;
regiospecific im-derivatization.
;
Chemistry
;
Biochemistry and Biotechnology
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A report claiming that AcHisOMe reacts regiospecifically with 4-fluoronitrobenzene to give AcHis[τPh(NO2)]OMe, which on treatment with H2/Pd(C) undergoes a partial τ-π shift to give some AcHis[πPh(NH2)]OMe, cannot be substantiated. 4(5)-Methylimidazole, a model for AcHisOMe, gives on reaction with 4-fluoronitrobenzene a 4:1 mixture of the regioisomers 1-(4-nitrophenyl),4-methylimidazole, corresponding to τ-substitution, and 1-(4-nitrophenyl),5-methylimidazole, corresponding to π-substitution, each of which has been isolated and fully characterized, including proof of orientation. In both cases, treatment with H2/Pd(C) gives a single product, without any change of orientation in either case. © 1997 European Peptide Society and John Wiley & Sons, Ltd.J. Pep. Sci.3: 391-394No. of Figures: 2. No. of Tables: 0. No. of References: 9
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
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