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Synthesis and spectroscopic characterization of protected N ‐phosphonomethylglycine dipeptides
Author(s) -
Ziora Zyta,
Kafarski Paweł,
Holband Jolanta,
Wójcik Grażyna
Publication year - 2001
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.340
Subject(s) - phosphonate , chemistry , conformational isomerism , peptide , peptide bond , stereochemistry , solid state , phosphorus , nuclear magnetic resonance spectroscopy , protecting group , combinatorial chemistry , organic chemistry , molecule , biochemistry , alkyl
Abstract A series of terminally blocked dipeptides containing C ‐terminal N ‐phosphonomethylglycine (glyphosate, an extremely effective non‐selective post‐emergence herbicide) have been synthesized by a solution method. The presence of their two conformers, cis ( syn ) and trans ( anti ), was shown in solutions by NMR spectroscopy. Molecular structures of the peptides were also determined in the solid state by X‐ray diffraction. The attempts for the selective and total removal of the groups protecting amino, carboxylic and phosphonate functions were in many cases unsuccessful due to the formation of cyclic structures and breakage of the phosphorus‐to‐carbon bond. Copyright © 2001 European Peptide Society and John Wiley & Sons, Ltd.