Synthesis and nmr conformational studies of polyoxyethylene-bound, alpha-deuterated glutamate oligopeptides |
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Authors: | A A Ribeiro R Saltman M Goodman |
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Abstract: | The syntheses of three series of glutamate oligopeptides attached to a macromolecular solubilizing polyoxyethylene (POE) group Boc-[Glu(OMe)]n-OPOE, Ac-[Glu(OMe)]n-OPOE, pGlu-[Glu(OMe)]n?1-OPOE (n ? 1–7) and their various analogs specifically deuterated at individual α-CH positions using the liquid-phase method of peptide synthesis are described. It was shown that stepwise synthesis using the symmetrical anhydride gave homo-oligopeptides that are analytically pure. Fragment condensation methods using DCC-HOBt yield POE-peptides with POE-HOBt impurities but the peptide synthesis may be carried stoichiometrically with smaller quantities of amino acid derivatives. 360 MHz 1H-nmr conformational studies of these homo-oligopeptides in DMSO-d6 are presented. The α-deuterated peptides are shown to allow unequivocal homoligopeptide backbone NH assignments. |
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