Synthesis of N-alkyl-C α, α-dimethylglycine derivatives

Bibliographic Details
Main Author: Monteiro, Luís S.
Publication Date: 2014
Other Authors: Pereira-Lima, Sílvia M. M. A., Pereira, Sofia, Machado, João N
Format: Article
Language: eng
Source: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Download full: http://hdl.handle.net/1822/48102
Summary: The application of trialkyloxonium tetrafluoroborates for N-alkylation of the nonnatural amino acid Cα, α-dimethylglycine is described. Several methyl esters of dimethylglycine protected with different amine protecting groups were subject to N-ethylation or N-methylation with triethyloxonium tetrafluoroborate or trimethyloxonium tetrafluoroborate, respectively. The corresponding N-akyl-Cα, α-dimethylglycine derivatives were obtained in good to high yields. Removal of the methyl ester rendered amino acid derivatives ready for application in peptide synthesis.
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spelling Synthesis of N-alkyl-C α, α-dimethylglycine derivativesAmino acidsnonnatural amino acidsalkylationN-alkyl-Calphaalpha-dimethylglycinesThe application of trialkyloxonium tetrafluoroborates for N-alkylation of the nonnatural amino acid Cα, α-dimethylglycine is described. Several methyl esters of dimethylglycine protected with different amine protecting groups were subject to N-ethylation or N-methylation with triethyloxonium tetrafluoroborate or trimethyloxonium tetrafluoroborate, respectively. The corresponding N-akyl-Cα, α-dimethylglycine derivatives were obtained in good to high yields. Removal of the methyl ester rendered amino acid derivatives ready for application in peptide synthesis.Foundation for Science and Technology (FCT) – Portugal and Fundo Europeu de Desenvolvimento Regional (FEDER) for financial support to Chemistry Centre of University of Minho. The NMR spectrometer Bruker Avance II+ 400 is part of the National NMR Network and was purchased in the framework of the National Program for Scientific Re-equipment; contract REDE/1517/RMN/2005, with funds from POCI 2010, FEDER and FCT.info:eu-repo/semantics/publishedVersionARKAT USA, Inc.Universidade do MinhoMonteiro, Luís S.Pereira-Lima, Sílvia M. M. A.Pereira, SofiaMachado, João N20142014-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/48102engLuís S. Monteiro, Silvia M. M. A. Pereira-Lima, Sofia Pereira, and João N. Machado, ARKIVOC 2014 (v) 170-1801551-70121551-700410.3998/ark.5550190.p008.622http://www.arkat-usa.org/get-file/51110info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-07-21T12:34:29Zoai:repositorium.sdum.uminho.pt:1822/48102Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T19:30:10.774917Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Synthesis of N-alkyl-C α, α-dimethylglycine derivatives
title Synthesis of N-alkyl-C α, α-dimethylglycine derivatives
spellingShingle Synthesis of N-alkyl-C α, α-dimethylglycine derivatives
Monteiro, Luís S.
Amino acids
nonnatural amino acids
alkylation
N-alkyl-Calpha
alpha-dimethylglycines
title_short Synthesis of N-alkyl-C α, α-dimethylglycine derivatives
title_full Synthesis of N-alkyl-C α, α-dimethylglycine derivatives
title_fullStr Synthesis of N-alkyl-C α, α-dimethylglycine derivatives
title_full_unstemmed Synthesis of N-alkyl-C α, α-dimethylglycine derivatives
title_sort Synthesis of N-alkyl-C α, α-dimethylglycine derivatives
author Monteiro, Luís S.
author_facet Monteiro, Luís S.
Pereira-Lima, Sílvia M. M. A.
Pereira, Sofia
Machado, João N
author_role author
author2 Pereira-Lima, Sílvia M. M. A.
Pereira, Sofia
Machado, João N
author2_role author
author
author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Monteiro, Luís S.
Pereira-Lima, Sílvia M. M. A.
Pereira, Sofia
Machado, João N
dc.subject.por.fl_str_mv Amino acids
nonnatural amino acids
alkylation
N-alkyl-Calpha
alpha-dimethylglycines
topic Amino acids
nonnatural amino acids
alkylation
N-alkyl-Calpha
alpha-dimethylglycines
description The application of trialkyloxonium tetrafluoroborates for N-alkylation of the nonnatural amino acid Cα, α-dimethylglycine is described. Several methyl esters of dimethylglycine protected with different amine protecting groups were subject to N-ethylation or N-methylation with triethyloxonium tetrafluoroborate or trimethyloxonium tetrafluoroborate, respectively. The corresponding N-akyl-Cα, α-dimethylglycine derivatives were obtained in good to high yields. Removal of the methyl ester rendered amino acid derivatives ready for application in peptide synthesis.
publishDate 2014
dc.date.none.fl_str_mv 2014
2014-01-01T00:00:00Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/1822/48102
url http://hdl.handle.net/1822/48102
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Luís S. Monteiro, Silvia M. M. A. Pereira-Lima, Sofia Pereira, and João N. Machado, ARKIVOC 2014 (v) 170-180
1551-7012
1551-7004
10.3998/ark.5550190.p008.622
http://www.arkat-usa.org/get-file/51110
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv ARKAT USA, Inc.
publisher.none.fl_str_mv ARKAT USA, Inc.
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
repository.mail.fl_str_mv
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