Mechanism of dansylation of the polyamine pentaazapentacosane ·5 HCl

Autor:	Yung Chi Lee, Samuel H. Yalkowsky, Susan Heimbecher, S. Esmail Tabibi
Rok vydání:	1998
Předmět:	chemistry.chemical_compound Chromatography chemistry Kinetics Dansyl chloride Pharmaceutical Science A value Molecule Amine gas treating Piperidine Polyamine High-performance liquid chromatography
Zdroj:	International Journal of Pharmaceutics. 160:21-29
ISSN:	0378-5173
DOI:	10.1016/s0378-5173(97)00315-3
Popis:	Dansylation of the pentaamine pentaazapentacosane ·5 HCl (PAPC) produces only the perdansyl product. This occurs even under conditions of pH and dansyl chloride concentration most likely to produce partially dansylated products. This result is explained by a mechanism whereby only completely unionized amine molecules will dansylate. The proposed mechanism is supported by the dansylation versus pH profile of PAPC versus that of a reference monoamine (piperidine ·HCl). After 4 h at room temperature and pH 9.5, 100% of piperidine is dansylated while under the same conditions only 10% of PAPC is derivatized. A pH greater than 10.5 is required to completely dansylate PAPC. This difference is significantly greater than would be predicted from the p K a values but it is consistent with the proposed mechanism.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::500744ded9b62f2f4655182091295d72 https://doi.org/10.1016/s0378-5173(97)00315-3 Zobrazit plný text záznamu Full Text from ScienceDirect