Novel sulfur and selenium containing bis-alpha-amino acids from 4-hydroxyproline.
The synthesis of new substituted prolines carrying at C-4 a second alpha-amino acid residue is reported. The amino acid, L-cysteine or L-selenocysteine, is linked to the proline ring through the sulfur or the selenium atom, respectively. The products were prepared with different stereochemistry at C-4, in few and clean high-yielding steps, with suitable protections for solid phase applications. The introduction of both sulfur and selenium atoms at C-4 of the proline ring seems to enhance significantly the cis geometry at the prolyl amide bond.
Caputo
Romualdo
R
Dipartimento di Chimica Organica e Biochimica, Università di Napoli Federico II, 80126, Naples, Italy.
Dellagreca
Marina
M
de Paola
Ivan
I
Mastroianni
Domenico
D
Longobardo
Luigi
L
D003545:Cysteine / Q000737:chemistry*; D006909:Hydroxyproline / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D012643:Selenium / Q000737:chemistry*; D013237:Stereoisomerism; D013455:Sulfur / Q000737:chemistry*
D013455:Sulfur; D012643:Selenium; D003545:Cysteine; D006909:Hydroxyproline