Highly parallel nano-synthesis of cleavable peptide-dye conjugates on cellulose membranes

Tetrahedron Letters

Volumn 41, Issue 11, 2000, Pages 1711-1715

  Licha, Kai ^a   Bhargava, Sarah ^b   Rheinländer, Christiane ^a   Becker, Andreas ^a   Schneider Mergener, Jens ^b   Volkmer Engert, Rudolf ^b  

^a Inst Diagnostikforschung An F   (Germany)

^b CHARITÉ UNIVERSITÄTSMEDIZIN BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; CELLULOSE; CONTRAST MEDIUM; CYANINE DYE; FLUORESCENT DYE; PEPTIDE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CONJUGATE; DRUG STRUCTURE; DRUG SYNTHESIS; MEMBRANE; REACTION ANALYSIS;

EID: 0034635844     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00019-8     Document Type: Article

References (20)

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3. Abbreviations: CAPE: cellulose-amino-hydroxypropyl ether; DBF: dibenzofulvene; DIEA: diisopropylethylamine; DCM: dichloromethane; HMB: 4-hydroxymethylbenzoic acid; NMI: N-methylimidazole; NTB: 2-nitro-5-thiobenzoate; TFA: trifluoroacetic acid; TBTU: O-(Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium- tetrafluoroborate; TIBS: tri-isobutylsilane.
4. Heveker, N.; Montes, M.; Germeroth, L.; Amara, A.; Trautmann, A.; Alizon, M.; Schneider-Mergener, J. Curr. Biol. 1998, 8, 369-376.
5. Hoffmüller, U.; Russwurm, M.; Kleinjung, F.; Ashurst, J.; Oschkinat, H.; Volkmer-Engert, R.; Koesling, D.; Schneider-Mergener, J. Angew. Chem., Int. Ed. Engl. 1999, 38, 2000-2004.
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11. 302=8100).
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14. 3 (2 min), followed by washing steps including water, ethanol and ether. S-Alkylation with the Fmoc-amino acid 3-bromopropyl esters (1.2 μl of a 0.6 M solution in DMF per spot, double coupling, 15 min each). Coupling yields were determined by measuring the absorbance of the released Fmoc-group.
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16. 4) and evaporated in vacuo. Yields of the 3-bromopropyl esters were in the range of 89-95% as determined by RP-HPLC. The Fmoc-Arg(Pmc) 3-bromo-propylester was prepared by esterification of Fmoc-Arg(Pmc)-OH using 1 equiv. 1-bromo-3-propanol, 1.1 equiv. DCC, 2 equiv. NMI and DCM as solvent. The resulting ester was isolated after 12 h in 79% yield.
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20. Before punching out the spots, the membrane was washed with phosphate buffer (0.1 M, pH 7.5), water, ethanol and dried. A single spot was incubated with a mixture containing 50 μl of methanol, 100 μl of water and 50 μl of a 0.5 M methanolic solution of sodium methanolate.