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Org Lett ; 22(20): 8039-8043, 2020 10 16.
Article in English | MEDLINE | ID: mdl-33006475

ABSTRACT

Sustainable and efficient manufacturing methods for N-methylated peptides remain underexplored despite growing interest in therapeutic N-methylated peptides within the pharmaceutical industry. A methodology for the coupling of C-terminally unprotected N-methylamino acids mediated by an isostearic acid halide (ISTAX) and silylating reagent has been developed. This approach allows for the coupling of a wide variety of amino acids and peptides in high yields under mild conditions without the need for a C-terminal deprotection step in the process of C-terminal elongation. These advantages make this a useful synthetic method for the production of peptide therapeutics and diagnostics containing N-methylamino acids.


Subject(s)
Anhydrides/chemistry , Indicators and Reagents/chemistry , Peptides/chemistry , Amino Acids , Molecular Structure , Stereoisomerism
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