2012
DOI: 10.1111/j.1747-0285.2011.01303.x
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Cysteinoyl‐ and Cysteine‐containing Dipeptidoylbenzotriazoles with Free Sulfhydryl Groups: Easy Access to N‐terminal and Internal Cysteine Peptides

Abstract: N‐Protected cysteines 4a–c each with a free sulfhydryl group were prepared in 70–75% yields by treatment of l‐cysteine with 1‐(benzyloxycarbonyl) benzotriazole (Cbz‐Bt) 1a, N‐(tert‐butyloxy‐carbonyl)benzotriazole (Boc‐Bt) 1b, and 1‐(9‐fluorenylmethoxy‐carbonyl)benzotriazole (Fmoc‐Bt) 1c, respectively. N‐Protected, free sulfhydryl cysteines 4a–c were then converted into the corresponding N‐protected, free sulfhydryl cysteinoylbenzotriazoles 7a–c (70–85%), which on treatment with diverse amino acids and dipeptid… Show more

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Cited by 4 publications
(3 citation statements)
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“…Subsequently, a condensation reaction involving compound 3 with (±)‐cysteine was performed, resulting in the formation of key intermediate 4 . Treatment of compound 4 with 1‐hydroxy benzotriazole (HOBt) in the presence of condensing agent 1‐ethyl‐3‐(3‐dimethylpropylamine) carbodiimide (EDCI) generated active ester 5 (Ibrahim et al., 2012). Finally, the target molecules were prepared by the reaction of 5 with N ‐alkylbenzylamines ( 6–8 ) (Contreras et al., 1999).…”
Section: Resultsmentioning
confidence: 99%
“…Subsequently, a condensation reaction involving compound 3 with (±)‐cysteine was performed, resulting in the formation of key intermediate 4 . Treatment of compound 4 with 1‐hydroxy benzotriazole (HOBt) in the presence of condensing agent 1‐ethyl‐3‐(3‐dimethylpropylamine) carbodiimide (EDCI) generated active ester 5 (Ibrahim et al., 2012). Finally, the target molecules were prepared by the reaction of 5 with N ‐alkylbenzylamines ( 6–8 ) (Contreras et al., 1999).…”
Section: Resultsmentioning
confidence: 99%
“…1‐Benzyloxycarbonyl‐1 H ‐benzo[ d ][1.2.3]triazole (4g): The reaction was carried out as described in the general procedure using N ‐benzyloxycarbonyl‐1,2‐phenylenediamine ( 3g ) (0.148 g, 0.611 mmol), polymer‐supported nitrite (0.524 g, containing 1.83 mmol of NO 2 ) and p ‐toluenesulfonic acid monohydrate (0.315 g, 1.83 mmol). The reaction was complete after 1.5 h. Purification by silica gel flash column chromatography eluting with 20 % diethyl ether in hexane gave 1‐benzyloxycarbonyl‐1 H ‐benzo[ d ][1.2.3]triazole ( 4g ) (0.102 g, 66 %) as a white solid.…”
Section: Methodsmentioning
confidence: 99%
“…The reaction was complete after 1.5 h. Purification by silica gel flash column chromatography eluting with 20 % diethyl ether in hexane gave 1‐benzyloxycarbonyl‐1 H ‐benzo[ d ][1.2.3]triazole ( 4g ) (0.102 g, 66 %) as a white solid. Mp 108–110 °C (lit . 108–110 °C).…”
Section: Methodsmentioning
confidence: 99%