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One-pot isomerization-cross metathesis-reduction (ICMR) synthesis of lipophilic tetrapeptides.

ABSTRACT: 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.

SUBMITTER: Jida M

PROVIDER: S-EPMC4140390 | biostudies-literature | 2014 Jul

REPOSITORIES: biostudies-literature

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One-pot isomerization-cross metathesis-reduction (ICMR) synthesis of lipophilic tetrapeptides.

Jida Mouhamad M Betti Cecilia C Schiller Peter W PW Tourwé Dirk D Ballet Steven S

ACS combinatorial science 20140618 7

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 alkyl ...[more]

PMID: 24906051

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