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

[Image: see text] 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(4)-promoted substitution reaction between a primary amine and a chloromethyl-functionalized thiazole or oxazole. T...

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Autores principales: Motevalli, Somayeh, Nguyen, Michelle T., Tan, Jiacheng, Fuller, Amelia A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6977196/
https://www.ncbi.nlm.nih.gov/pubmed/31984279
http://dx.doi.org/10.1021/acsomega.9b03682
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author Motevalli, Somayeh
Nguyen, Michelle T.
Tan, Jiacheng
Fuller, Amelia A.
author_facet Motevalli, Somayeh
Nguyen, Michelle T.
Tan, Jiacheng
Fuller, Amelia A.
author_sort Motevalli, Somayeh
collection PubMed
description [Image: see text] 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(4)-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.
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spelling pubmed-69771962020-01-24 Diverse N-Substituted Azole-Containing Amino Acids as Building Blocks for Cyclopeptides Motevalli, Somayeh Nguyen, Michelle T. Tan, Jiacheng Fuller, Amelia A. ACS Omega [Image: see text] 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(4)-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. American Chemical Society 2020-01-08 /pmc/articles/PMC6977196/ /pubmed/31984279 http://dx.doi.org/10.1021/acsomega.9b03682 Text en Copyright © 2020 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Motevalli, Somayeh
Nguyen, Michelle T.
Tan, Jiacheng
Fuller, Amelia A.
Diverse N-Substituted Azole-Containing Amino Acids as Building Blocks for Cyclopeptides
title Diverse N-Substituted Azole-Containing Amino Acids as Building Blocks for Cyclopeptides
title_full Diverse N-Substituted Azole-Containing Amino Acids as Building Blocks for Cyclopeptides
title_fullStr Diverse N-Substituted Azole-Containing Amino Acids as Building Blocks for Cyclopeptides
title_full_unstemmed Diverse N-Substituted Azole-Containing Amino Acids as Building Blocks for Cyclopeptides
title_short Diverse N-Substituted Azole-Containing Amino Acids as Building Blocks for Cyclopeptides
title_sort diverse n-substituted azole-containing amino acids as building blocks for cyclopeptides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6977196/
https://www.ncbi.nlm.nih.gov/pubmed/31984279
http://dx.doi.org/10.1021/acsomega.9b03682
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