Relative Reactivities of Activated Carboxylic Acids in Amide-Forming Reactions Employed for the Synthesis of Tetraphenylporphyrin Libraries
| Autor: | Kendra L. Dombi, Clemens Richert |
|---|---|
| Rok vydání: | 2000 |
| Předmět: |
Porphyrins
Pharmaceutical Science Peptide Cleavage (embryo) Mass spectrometry Analytical Chemistry lcsh:QD241-441 chemistry.chemical_compound lcsh:Organic chemistry Amide Drug Discovery Polymer chemistry Tetraphenylporphyrin Organic chemistry Reactivity (chemistry) Physical and Theoretical Chemistry chemistry.chemical_classification Chemistry mixed couplings Organic Chemistry Porphyrin Combinatorial chemistry reactivity Chemistry (miscellaneous) combinatorial chemistry Molecular Medicine |
| Zdroj: | Molecules, Vol 5, Iss 12, Pp 1265-1280 (2000) Molecules; Volume 5; Issue 12; Pages: 1265-1280 |
| DOI: | 10.3390/ecsoc-4-01909 |
| Popis: | Electronic Conference on Synthetic Organic Chemistry (ECSOC-4), September 1-30, 2000, (Paper C0016).*To whom correspondence should be addressed. E-mail: Clemens.Richert@uni-konstanz.deReceived: 3 November 2000 / Accepted: 17 November 2000 / Published: 18 December 2000Abstract: Presented here is a method for rapidly testing the reactivity of carboxylic acids inamide-forming reactions. For this, a mixture of two acids, one a reference compound, andone acid whose reactivity is unknown, are coupled to an aminoacylated tetrakis(p-aminophenyl)porphyrin under typical peptide coupling conditions. The product distributionin the resulting library is analyzed via MALDI-TOF mass spectrometry to reveal the relativereactivity. This rapid reactivity test requires sub-nanomole quantities of acids, does notinvolve cleavage from a support or any potentially biasing work-up, and is automatable.Thus, it is well suited for testing building blocks for combinatorial syntheses. Further, it isdemonstrated that step-wise coupling can produce near-statistically distributed libraries ofporphyrins when acids of very different reactivity are employed.Keywords: Porphyrins, combinatorial chemistry, reactivity, mixed couplings |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|