Synthetic studies on stevastelins. 2. Synthesis of lipidic- and peptidic-modified analogues.
[Chemical reaction: See text] The synthesis of a series of stevastelin analogues with modification of the susbstituent at the C-2 position of the stearic acid chain (compounds 28 and 31), variation of the amino acids (compounds 41, 42, 73, and 78), or lacking the lipidic chain (compound 91) is described. The replacement of L-valine and L-threonine with other amino acids proceeded without difficulties for the synthesis of analogues 41 and 42; however, the substitution of L-serine with simple amino acids, such as glycine or L-alanine, proved to be elusive, which was adscribed to factors of conformational flexibility. Finally, the substitution with L-valine or L-threonine proceeded without difficulties to provide the analogues 73 and 78 respectively.
Sarabia
Francisco
F
Department of Biochemistry, Molecular Biology and Organic Chemistry, Faculty of Sciences, University of Malaga, Campus de Teatinos s/n, 29071, Malaga, Spain. frsarabia@uma.es
Chammaa
Samy
S
García-Castro
Miguel
M
D000478:Alkylation; D000595:Amino Acid Sequence; D019943:Amino Acid Substitution; D047630:Depsipeptides / Q000138:chemical synthesis*; D005656:Fungal Proteins / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis / Q000737:chemistry; D013229:Stearic Acids / Q000138:chemical synthesis
D047630:Depsipeptides; D005656:Fungal Proteins; D007202:Indicators and Reagents; D010455:Peptides; D010456:Peptides, Cyclic; D013229:Stearic Acids; C100705:stevastelin B