Application of N,N-dimethylformamide dineopentyl acetal for efficient anchoring of N alpha-9-fluorenylmethyloxycarbonylamino acids as p-alkoxybenzyl esters in solid-phase peptide synthesis.
The attachment of Fmoc-amino acids onto p- alkoxybenzyl alcohol resins via DCC-DMAP coupling suffers from two different problems: formation of dimers and racemization. The use of N,N-dimethylformamide dineopentyl acetal for the preparation of Fmoc- aminoacyloxybenzyl handles is the basis of a safe and efficient anchoring method that avoids both problems.
D015761:4-Aminopyridine / Q000031:analogs & derivatives*; D000080:Acetals; D000596:Amino Acids; D000631:Aminopyridines; D001592:Benzyl Alcohols; D055598:Chemical Phenomena; D002621:Chemistry; D004024:Dicyclohexylcarbodiimide; D005449:Fluorenes; D010455:Peptides / Q000138:chemical synthesis*
D000080:Acetals; D000596:Amino Acids; D000631:Aminopyridines; D001592:Benzyl Alcohols; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D010455:Peptides; C041646:N,N-dimethylformamide dineopentyl acetal; D004024:Dicyclohexylcarbodiimide; D015761:4-Aminopyridine; C003885:4-dimethylaminopyridine