ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Nα[(tert-Butoxy)carbonyl]-2-diazo-L-histidine methyl ester 1 was synthesized starting from the corresponding L-histidine derivative. The physico-chemical properties of this new photoactivatable amino-acid derivative were established. The synthetic precursor of 1, 2-amino-L-histidine derivative 3, was best isolated and characterized as 2-amino-Nα-[(tert-butoxy)carbonyl]-Nτ-tosyl-L-histidine methyl ester (4). Selective deprotections of 4 (Nα-Boc, Nα-Tos, COOMe) were achieved, thus allowing the use of the corresponding products in peptide synthesis. The optically active dipeptides 8 and 9 were synthesized by coupling 2-amino-Nτ-tosyl-L-histidine methyl ester (5) with N-[(tert-butoxy)carbonyl]-L-alanine and Nα-[(tert-butoxy)carbonyl]-Nτ-tosyl-L-histidine (6) with L-alanine methyl ester, respectively. The question of selective diazotization of a 2-aminohistidine residue in a synthetic peptide was studied using competitive diazotizations between 2-amino-1H-imidazole and several amino-acid derivatives susceptible to undergo nitrosylation. The results show that synthetic photoactivatable peptides incorporating a 2-diazohistidine residue might become useful photoaffinity probes.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19900730109
