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Solution-phase synthesis of novel seven-membered cyclic dipeptides containing α- and β-amino acids
- Source :
-
Tetrahedron . Nov2012, Vol. 68 Issue 47, p9842-9852. 11p. - Publication Year :
- 2012
-
Abstract
- Abstract: A convenient synthetic procedure for the preparation of seven-membered cyclic α,β-dipeptides is described. Following coupling of N-protected α-amino acids with N-substituted β-amino acid tert-butyl esters, that affords linear α,β-dipeptides, the protecting groups at the terminal functionalities were removed and the open-chain dipeptides were cyclized with phenylphosphonic dichloride, PhP(O)Cl2, to give the desired cyclic α,β-dipeptides in good yields. NMR studies, X-ray diffraction analysis, and DFT calculations provided evidence for the conformation adopted by these cyclic dipeptides in solution, in the solid-state, and in the gas phase. [Copyright &y& Elsevier]
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 68
- Issue :
- 47
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 82499435
- Full Text :
- https://doi.org/10.1016/j.tet.2012.08.050