Reversible Aminal Formation: Controlling the Evaporation of Bioactive Volatiles by Dynamic Combinatorial/Covalent Chemistry

被引:61
作者
Buchs , Barbara [1 ]
Godin, Guillaume [1 ]
Trachsel, Alain [1 ]
de Saint Laumer, Jean-Yves [1 ]
Lehn, Jean-Marie [2 ]
Herrmann, Andreas [1 ]
机构
[1] Firmenich Co, Div Rech & Dev, CH-1211 Geneva 8, Switzerland
[2] Univ Strasbourg, ISIS, F-67083 Strasbourg, France
关键词
Aminals; Combinatorial chemistry; Controlled release; Fragrances; Retro reactions; CONTROLLED-RELEASE; COVALENT CHEMISTRY; SUPRAMOLECULAR CHEMISTRY; ASYMMETRIC-SYNTHESIS; HEXAHYDROPYRIMIDINES; AMPLIFICATION; DERIVATIVES; COMPLEXES; LIBRARIES; EXCHANGE;
D O I
10.1002/ejoc.201001433
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dynamic mixtures generated by reversible aminal formation efficiently prolong the duration of evaporation of bioactive volatile aldehydes. Secondary diamines used for the generation of dynamic mixtures are obtained by treatment of primary diamines with carbonyl compounds and reduction of the diimines with NaBH4. The reversibilities of the reactions were demonstrated by NMR measurements in buffered aqueous solutions. Kinetic rate constants and equilibrium constants for the formation and hydrolysis of aminals were determined. The performance of dynamic mixtures as delivery systems for perfumery ingredients was tested after deposition onto cotton, and the long-lastingness of fragrance evaporation was investigated by dynamic headspace analysis against a reference sample. The simplicity of the concept together with its excellent performance makes this delivery system highly interesting for applied perfumery. Reversible aminal formation might also be successfully applicable to dynamic combinatorial/covalent chemistry for screening of pharmaceutically or catalytically active ligands and receptors.
引用
收藏
页码:681 / 695
页数:15
相关论文
共 113 条
[1]  
ALEXAKIS A, 1995, SYNTHESIS-STUTTGART, P1038
[2]   Chiral aminals: Powerful auxiliaries in asymmetric synthesis [J].
Alexakis, A ;
Mangeney, P ;
Lensen, N ;
Tranchier, JP ;
Gosmini, R ;
Raussou, S .
PURE AND APPLIED CHEMISTRY, 1996, 68 (03) :531-534
[3]  
Alexakis A., 1996, ADV ASYMMETRIC SYNTH, P93
[4]  
[Anonymous], 2010, ANGEW CHEM
[5]   Dynamic interactive systems: dynamic selection in hybrid organic-inorganic constitutional networks [J].
Barboiu, Mihail .
CHEMICAL COMMUNICATIONS, 2010, 46 (40) :7466-7476
[6]   The asymmetric synthesis of alpha-substituted alpha-methyl and alpha-phenyl phosphonic acids: Design, carbanion geometry, reactivity and preparative aspects of chiral alkyl bicyclic phosphonamides [J].
Bennani, YL ;
Hanessian, S .
TETRAHEDRON, 1996, 52 (44) :13837-13866
[7]   Facile acetal dynamic combinatorial library [J].
Berkovich-Berger, Dvora ;
Lemcoff, N. Gabriel .
CHEMICAL COMMUNICATIONS, 2008, (14) :1686-1688
[8]   Influence of the Backbone Structure on the Release of Bioactive Volatiles from Maleic Acid-Based Polymer Conjugates [J].
Berthier, Damien L. ;
Paret, Nicolas ;
Trachsel, Alain ;
Herrmann, Andreas .
BIOCONJUGATE CHEMISTRY, 2010, 21 (11) :2000-2012
[9]   Affinity chromatography in dynamic combinatorial libraries: one-pot amplification and isolation of a strongly binding receptor [J].
Besenius, Pol ;
Cormack, Peter A. G. ;
Ludlow, R. Frederick ;
Otto, Sijbren ;
Sherrington, David C. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (10) :2414-2418
[10]  
Bhat VT, 2010, NAT CHEM, V2, P490, DOI [10.1038/NCHEM.658, 10.1038/nchem.658]