原创力文档relative reactivities of activated carboxylic acids in amide-forming reactions employed for the synthesis of tetraphenylporphyrin libraries相对反应活性的激活在amide-forming羧酸反应用于合成tetraphenylporphyrin库.pdfVIP
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relative reactivities of activated carboxylic acids in amide-forming reactions employed for the synthesis of tetraphenylporphyrin libraries相对反应活性的激活在amide-forming羧酸反应用于合成tetraphenylporphyrin库
Molecules 2000, 5, 1265–1280
molecules
ISSN 1420-3049
Relative Reactivities of Activated Carboxylic Acids in Amide-
Forming Reactions Employed for the Synthesis of
Tetraphenylporphyrin Libraries‡
Kendra L. Dombi and Clemens Richert*
Departments of Chemistry, Tufts University, Medford MA, 02155, USA and University of Constance,
Fach 709, D-78457 Konstanz, Germany.
‡ Presented at the 4th 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.de
Received: 3 November 2000 / Accepted: 17 November 2000 / Published: 18 December 2000
Abstract: Presented here is a method for rapidly testing the reactivity of carboxylic acids in
amide-forming reactions. For this, a mixture of two acids, one a reference compound, and
one acid whose reactivity is unknown, are coupled to an aminoacylated tetrakis(p-
aminophenyl)porphyrin under typical peptide coupling conditions. The product distribution
in the resulting library is analyzed via MALDI-TOF mass spectrometry to reveal the relative
reactivity. This rapid reactivity test requires sub-nanomole quantities of acids, does not
involve 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 is
demonstrated that step-wise coupling can produce near-statistically distributed libraries of
porphyrins when acids of very different reactivity are employed.
Keywords: Por
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