β-Silyl alkynoates: Versatile reagents for biocompatible and selective amide bond formation.

ABSTRACT: The study introduces a previously unidentified method for amide bond formation that addresses several limitations of conventional approaches. It uses the β-silyl alkynoate molecule, where the alkynyl group activates the ester for efficient amide formation, while the bulky TIPS (triisopropylsilane) group prevents unwanted 1,4-addition reactions. This approach exhibits high chemoselectivity for amines, making the method compatible with a wide range of substrates, including secondary amines, and targets the specific ε-amino group of lysine among the native amino ester's derivatives. It maintains stereochemistry during amide bond formation and TIPS group removal, allowing a versatile platform for postsynthesis modifications such as click reactions and peptide-drug conjugations. These advanceme

SUBMITTER: Choudhuri K 

PROVIDER: S-EPMC11421574 | biostudies-literature | 2024 Sep

REPOSITORIES: biostudies-literature