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Diverse N-Substituted Azole-Containing Amino Acids as Building Blocks for Cyclopeptides.

ABSTRACT: The preparation of 16 oxazole- or thiazole-containing amino esters bearing a wide array of N-substitution is reported. These were accessed in 40-92% yield via an AgClO4-promoted substitution reaction between a primary amine and a chloromethyl-functionalized thiazole or oxazole. These new synthetic building blocks will be useful for the preparation of new cyclopeptide analogues bearing heterocyclic backbone modifications. Four macrocyclic N-substituted oligoamides that include thiazole or oxazole heterocycles were obtained, following cyclooligomerization reactions of azole-modified N-substituted amino acids.

SUBMITTER: Motevalli S

PROVIDER: S-EPMC6977196 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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Diverse N-Substituted Azole-Containing Amino Acids as Building Blocks for Cyclopeptides.

Motevalli Somayeh S Nguyen Michelle T MT Tan Jiacheng J Fuller Amelia A AA

ACS omega 20200108 2

The preparation of 16 oxazole- or thiazole-containing amino esters bearing a wide array of N-substitution is reported. These were accessed in 40-92% yield via an AgClO<sub>4</sub>-promoted substitution reaction between a primary amine and a chloromethyl-functionalized thiazole or oxazole. These new synthetic building blocks will be useful for the preparation of new cyclopeptide analogues bearing heterocyclic backbone modifications. Four macrocyclic N-substituted oligoamides that include thiazole ...[more]

PMID: 31984279

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