One-Pot Isomerization–Cross Metathesis–Reduction (ICMR) Synthesis of Lipophilic Tetrapeptides

[Image: see text] An efficient, versatile and rapid method toward homologue series of lipophilic tetrapeptide derivatives (herein, the opioid peptides H-TIPP-OH and H-DIPP-OH) is reported. High atom economy and a minimal number of synthetic steps resulted from a one-pot tandem isomerization-cross me...

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Autores principales: Jida, Mouhamad, Betti, Cecilia, Schiller, Peter W., Tourwé, Dirk, Ballet, Steven
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4140390/
https://www.ncbi.nlm.nih.gov/pubmed/24906051
http://dx.doi.org/10.1021/co500020a
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author Jida, Mouhamad
Betti, Cecilia
Schiller, Peter W.
Tourwé, Dirk
Ballet, Steven
author_facet Jida, Mouhamad
Betti, Cecilia
Schiller, Peter W.
Tourwé, Dirk
Ballet, Steven
author_sort Jida, Mouhamad
collection PubMed
description [Image: see text] An efficient, versatile and rapid method toward homologue series of lipophilic tetrapeptide derivatives (herein, the opioid peptides H-TIPP-OH and H-DIPP-OH) is reported. High atom economy and a minimal number of synthetic steps resulted from a one-pot tandem isomerization-cross metathesis-reduction sequence (ICMR), applicable both in solution and solid phase methodology. The broadly applicable synthesis proceeds with short reaction times and simple work-up, as illustrated in this work for alkylated opioid tetrapeptides.
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spelling pubmed-41403902014-08-21 One-Pot Isomerization–Cross Metathesis–Reduction (ICMR) Synthesis of Lipophilic Tetrapeptides Jida, Mouhamad Betti, Cecilia Schiller, Peter W. Tourwé, Dirk Ballet, Steven ACS Comb Sci [Image: see text] An efficient, versatile and rapid method toward homologue series of lipophilic tetrapeptide derivatives (herein, the opioid peptides H-TIPP-OH and H-DIPP-OH) is reported. High atom economy and a minimal number of synthetic steps resulted from a one-pot tandem isomerization-cross metathesis-reduction sequence (ICMR), applicable both in solution and solid phase methodology. The broadly applicable synthesis proceeds with short reaction times and simple work-up, as illustrated in this work for alkylated opioid tetrapeptides. American Chemical Society 2014-06-06 2014-07-14 /pmc/articles/PMC4140390/ /pubmed/24906051 http://dx.doi.org/10.1021/co500020a Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Jida, Mouhamad
Betti, Cecilia
Schiller, Peter W.
Tourwé, Dirk
Ballet, Steven
One-Pot Isomerization–Cross Metathesis–Reduction (ICMR) Synthesis of Lipophilic Tetrapeptides
title One-Pot Isomerization–Cross Metathesis–Reduction (ICMR) Synthesis of Lipophilic Tetrapeptides
title_full One-Pot Isomerization–Cross Metathesis–Reduction (ICMR) Synthesis of Lipophilic Tetrapeptides
title_fullStr One-Pot Isomerization–Cross Metathesis–Reduction (ICMR) Synthesis of Lipophilic Tetrapeptides
title_full_unstemmed One-Pot Isomerization–Cross Metathesis–Reduction (ICMR) Synthesis of Lipophilic Tetrapeptides
title_short One-Pot Isomerization–Cross Metathesis–Reduction (ICMR) Synthesis of Lipophilic Tetrapeptides
title_sort one-pot isomerization–cross metathesis–reduction (icmr) synthesis of lipophilic tetrapeptides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4140390/
https://www.ncbi.nlm.nih.gov/pubmed/24906051
http://dx.doi.org/10.1021/co500020a
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