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1980•Journal of Medicinal ChemistryRequires access

Peptide sweeteners. 3. Effect of modifying the peptide bond on the sweet taste of L-aspartyl-L-phenylalanine methyl ester and its analogs

Scott Macdonald, C. Grant Willson, Michael Chorev, Fred S. Vernacchia, Murray Goodman

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Abstract

A series of analogues designed to assess the importance of the amide bond in the dipeptide sweetener L-aspartyl-L-phenylalanine methyl ester has been synthesized and tested. The peptide bond was methylated, replaced by an ester bond, or reversed. all of these modifications produced compounds that did not have a sweet taste. We conclude that the steric, electronic, and directional characteristics of the amide bond are essential for biological activity in the dipeptide sweeteners.

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What this paper is about

A series of analogues designed to assess the importance of the amide bond in the dipeptide sweetener L-aspartyl-L-phenylalanine methyl ester has been synthesized and tested. The peptide bond was methylated, replaced by an ester bond, or reversed. all of these modifications produced compounds that did not have a sweet taste. We conclude that the steric, electronic, and directional characteristics of the amide bond are essential for biological activity in the dipeptide sweeteners.

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Available abstract

A series of analogues designed to assess the importance of the amide bond in the dipeptide sweetener L-aspartyl-L-phenylalanine methyl ester has been synthesized and tested. The peptide bond was methylated, replaced by an ester bond, or reversed. all of these modifications produced compounds that did not have a sweet taste. We conclude that the steric, electronic, and directional characteristics of the amide bond are essential for biological activity in the dipeptide sweeteners.

Key concepts: Dipeptide, Chemistry, Peptide bond, Steric effects, Peptide, Phenylalanine, Stereochemistry, Aspartame

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Peptide sweeteners. 3. Effect of modifying the peptide bond on the sweet taste of L-aspartyl-L-phenylalanine methyl ester and its analogs — Research Paper | ScholarLens