Tetrahedron p. 4377 - 4382 (1989)
Update date:2022-08-04
Topics:
Mapelli, Claudio
Elrod, Luther F.
Holt, Elizabeth M.
Stammer, Charles H.
Details of the synthesis of 2,3-methanopyroglutamic acid (1), its N-methylamide (7) and N-β-naphthylamide (6) are reported.An NMR study of the conformation of 7 is discussed and the stability of the amide 6 to pyroglutamylaminopeptidase is detailed.The crystal structure of an alkene (4) formed during the pyrolysis of an intermediate pyrazoline (2) indicates that the (Z)-configuration is conserved during nitrogen extrusion.
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