Polymer-bound mixed carboxylic anhdrides as a stable form of act

Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – Synthesis of peptides

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530333, 530334, 562887, 562894, A62K 3802

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055168922

ABSTRACT:
Polymer-bound mixed carboxylic anhydrides can be prepared under mild conditions by the condensation of carboxylic acids (including N-protected amino acids) with polymer-bound acid chlorides. These mixed anhydrides function as polymeric reagents in the sense that they will react readily with monomeric nucleophiles such as amines to form amide or peptide products, depending on the identities of the mixed anhydride and amine reactants. However, in spite of their reactivity, these polymeric mixed anhydrides exhibit a significant degree of stability under conditions of prolonged storage, which suggests that such compounds have commercial utility as a relatively stable form of highly activated carboxylic acids. The polymeric support can be reactivated and recycled for repeated use in the derivatization process.

REFERENCES:
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M. B.Shambhu, G. A. Digenis, "Insoluble Resins in Organic Syntheses I. Preparation and Reactions of Polymeric Anhydrides," Tetrahedron Letters No. 18, pp. 1627-1629, 1973.
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V. K. Haridasan, A. Ajayaghosh, V. N. R. Pillai, "Polymer-Bound Mixed Carboxylic Dithiocarbamic Anhydrides. A New Class of Selective and Recyclable Soldi-Phase Acylating Reagents," J. Org. Chem., 1987, 52, 2662-2665.
Martin J Org Chem 43, 4571, 1978.

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