88950-65-6Relevant academic research and scientific papers
Synthesis and Taste Properties of L-Aspartyl-Methylated 1-Aminocyclopropanecarboxylic Acid Methyl Esters
Zhu, Yun-Fei,Yamazaki, Toshimasa,Tsang, Joseph W.,Lok, Stan,Goodman, Murray
, p. 1074 - 1081 (1992)
Several isomers of L-aspartyl-1-aminocyclopropanecarboxylic acid methyl ester with methyl group substitutions on the cyclopropane ring were synthesized.Conformational analyses were carried out on these molecules using 1H NMR and molecular modeling studies.Their taste properties are explained on the basis of our previously reported topochemical model for taste response.
Relative and absolute configuration of antitumor agent SW-163D
Nakaya, Mino,Oguri, Hiroki,Takahashi, Kosaku,Fukushi, Eri,Watanabe, Kenji,Oikawa, Hideaki
, p. 2969 - 2976 (2008/03/14)
Our interest on engineering non-ribosomal synthetase responsible for SW-163 biosynthesis prompted us to determine the relative and absolute configuration of antitumor cyclic depsipeptide SW-163s. We first isolated and identified SW-163 homologs D, F and G as known compounds UK-63598, UK-65662 and UK-63052, respectively. Both enantiomers of the unusual constitutive amino acid, N-methylnorcoromic acid, were synthesized in chiral forms starting from (R)- and (S)-1,2-propanediol. The hydrolyzate of SW-163D, a major constituent of this family, was converted with Marfey's reagent, 1-fluoro-2,4-dinitrophenyl-5-L- alanine-amide (L-FDAA), and the resulting mixture of amino acid derivatives was subjected to an LC/MS analysis. Compared with authentic samples, the analytical data unambiguously show that SW-163D consisted of L-Ala, D-Ser and (1S, 2S)-N-methylnorcoronamic acid. The remaining stereochemistry of the N-methylcysteine moieties was determined from NOE data.
A New Synthesis of Racemic Coronamic Acid and Other Cyclopropyl Amino Acids
Suzuki, M.,Gooch, E. E.,Stammer, C. H.
, p. 3839 - 3840 (2007/10/02)
A new method, in which various diazocompounds are added to a dehydro alanine derivative, allows the synthesis of coronamic acid and several other cyclopropyl amino acids.
