By a chemo-enzymatic approach we performed a large-scale, stereoselective synthesis of the Cα-methylated α-hydroxy acid L-(αMe)Hyv. We also prepared model depsipeptides based on this sterically demanding residue in combination with the α-amino acids L-Ala, L-Val, and Aib. From solution (FT-IR absorption and 1H NMR) and crystal-state (X-ray diffraction) conformational analyses we found that L-(αMe)Hyv forces depsipeptides to fold into right-handed β-turn/helical structures by analogy with the reported propensity of L-(αMe)Val, its α-amino acid counterpart.

Peggion C., Barazza A., Formaggio F., Crisma M., Toniolo C., Villa M., et al. (2002). (αMe)Hyv: Chemo-enzymatic synthesis, and preparation and preferred conformation of model depsipeptides. JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS 2, -(3), 644-651.

(αMe)Hyv: Chemo-enzymatic synthesis, and preparation and preferred conformation of model depsipeptides

Tomasini C.
Conceptualization
;
2002

Abstract

By a chemo-enzymatic approach we performed a large-scale, stereoselective synthesis of the Cα-methylated α-hydroxy acid L-(αMe)Hyv. We also prepared model depsipeptides based on this sterically demanding residue in combination with the α-amino acids L-Ala, L-Val, and Aib. From solution (FT-IR absorption and 1H NMR) and crystal-state (X-ray diffraction) conformational analyses we found that L-(αMe)Hyv forces depsipeptides to fold into right-handed β-turn/helical structures by analogy with the reported propensity of L-(αMe)Val, its α-amino acid counterpart.
2002
Peggion C., Barazza A., Formaggio F., Crisma M., Toniolo C., Villa M., et al. (2002). (αMe)Hyv: Chemo-enzymatic synthesis, and preparation and preferred conformation of model depsipeptides. JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS 2, -(3), 644-651.
Peggion C.; Barazza A.; Formaggio F.; Crisma M.; Toniolo C.; Villa M.; Tomasini C.; Mayrhofer H.; Pochlauer P.; Kaptein B.; Broxterman Q.B.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/914601
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