Tetrazoles as carboxylic acid surrogates in the suosan sweetener series
Related Experiment Video
Updated: Aug 12, 2026

Rapid One-step Enzymatic Synthesis and All-aqueous Purification of Trehalose Analogues
Published on: February 17, 2017
1Chemical Products Discovery, NutraSweet R & D, Mt. Prospect, IL 60056.
Abstract:
The structure-activity relationship (SAR) in the suosan series of sweeteners has been extended to include additional replacements for the carboxyl group. Tetrazole analogues have been prepared and were found to be sweet. However, both the urea and thiourea tetrazolyl analogues exhibited reduced potency when compared with the carboxyl compounds. Because of the larger size of tetrazole compared with carboxylic acid, chain-shortened tetrazolyl analogues were prepared and found to not be sweet. Some important aspects about the requirements for promoting a sweet taste in vivo can be gleaned from these results. The importance of the degree of delocalization and the orientation of charge density in the anionic group are discussed.
Related Concept Videos
Carboxylic Acid Derivatives: Overview
Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
Structures of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Preparation of Carboxylic Acids: Hydrolysis of Nitriles
Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives

