Cyclopropane amino acid ester dipeptide sweeteners
- 1 October 1987
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 30 (4) , 498-510
- https://doi.org/10.1111/j.1399-3011.1987.tb03358.x
Abstract
A series of esters of L-aspartyl-l-aminocyclopropane carboxylic acid has been prepared and their sweet tastes determined. The sweetest ester prepared was about 300 times sweeter than sucrose. An attempt to use basic conditions during preparation of the dipeptide allyl ester led to succinimide formation of the aspartyl peptide even though the .beta.-carboxyl group was protected by a t-butyl ester function. The X-ray structure of the propyl ester (1c) was determined and its conformation is discussed.Keywords
This publication has 19 references indexed in Scilit:
- Peptide homologs, isosteres, and isomers: A general approach to structure–activity relationshipsBiopolymers, 1985
- Peptide sweeteners. 6. Structural studies on the C-terminal amino acid of L-aspartyl dipeptide sweetenersJournal of Medicinal Chemistry, 1984
- Synthesis of (E)- and (Z)-cyclopropyl-3-chloroalanineThe Journal of Organic Chemistry, 1984
- Resolution and deblocking of racemic N-(benzyloxycarbonyl)-"cyclopropylphenylalanine"The Journal of Organic Chemistry, 1983
- 4‐Dialkylaminopyridines as Highly Active Acylation Catalysts. [New synthetic method (25)]Angewandte Chemie International Edition in English, 1978
- The structure-taste relationships of aspartyl dipeptide esters.Agricultural and Biological Chemistry, 1976
- Structure-taste relationships of L-aspartyl-aminomalonic acid diesters.CHEMICAL & PHARMACEUTICAL BULLETIN, 1976
- The Structure-Taste Relationships of the Dipeptide Esters Composed of l-Aspartic Acid and β-Hydroxy Amino AcidsBulletin of the Chemical Society of Japan, 1974
- Synthetic sweeteners. 3. Aspartyl dipeptide esters from L- and D-alkylglycinesJournal of Medicinal Chemistry, 1973
- Structure-taste relation of aspartic acid amidesJournal of Medicinal Chemistry, 1970