Convergent solution-phase synthesis of a nucleopeptide using a protected oligonucleotide

Dustin L. McMinn; Marc M. Greenberg

doi:10.1016/S0960-894X(99)00051-7

Convergent solution-phase synthesis of a nucleopeptide using a protected oligonucleotide

Dustin L. McMinn
, Marc M. Greenberg

Research output: Contribution to journal › Article › peer-review

Abstract

A nucleopeptide was prepared in a convergent manner via segmental coupling of the protected biopolymers in solution. The resulting nucleopeptide (4b, 72%) containing the binding site of λ repressor and a peptide containing the consensus sequence of the DNA binding helix of the helix turn-helix-proteins was obtained using only five equivalents of the peptide relative to the oligonucleotide. This demonstrates that the recently developed method for the solution phase coupling of protected oligonucleotides is amenable to the convergent synthesis of larger nucleopeptides that are potentially capable of adopting secondary structure.

Original language	English (US)
Pages (from-to)	547-550
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	9
Issue number	4
DOIs	https://doi.org/10.1016/S0960-894X(99)00051-7
State	Published - Feb 22 1999
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/S0960-894X(99)00051-7

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title = "Convergent solution-phase synthesis of a nucleopeptide using a protected oligonucleotide",

abstract = "A nucleopeptide was prepared in a convergent manner via segmental coupling of the protected biopolymers in solution. The resulting nucleopeptide (4b, 72\%) containing the binding site of λ repressor and a peptide containing the consensus sequence of the DNA binding helix of the helix turn-helix-proteins was obtained using only five equivalents of the peptide relative to the oligonucleotide. This demonstrates that the recently developed method for the solution phase coupling of protected oligonucleotides is amenable to the convergent synthesis of larger nucleopeptides that are potentially capable of adopting secondary structure.",

author = "McMinn, \{Dustin L.\} and Greenberg, \{Marc M.\}",

note = "Funding Information: Acknowledgments: We thank the National Science Foundation (CHE-9732843) for support of this research. Mass spectra were obtained on instrumentation supported by the National Institutes of Health shared instrumentation grant (GM-49631). D.L.M. and M.M.G. are grateful for fellowships from Boehringer-Ingelheim and the Alfred P. Sloan Foundation, respectively. We thank Professor Robert Woody and Dr. Narasimha Sreerama for their assistance with the CD experiments and for use of the CD spectrometer.",

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AU - McMinn, Dustin L.

AU - Greenberg, Marc M.

N1 - Funding Information: Acknowledgments: We thank the National Science Foundation (CHE-9732843) for support of this research. Mass spectra were obtained on instrumentation supported by the National Institutes of Health shared instrumentation grant (GM-49631). D.L.M. and M.M.G. are grateful for fellowships from Boehringer-Ingelheim and the Alfred P. Sloan Foundation, respectively. We thank Professor Robert Woody and Dr. Narasimha Sreerama for their assistance with the CD experiments and for use of the CD spectrometer.

PY - 1999/2/22

Y1 - 1999/2/22

N2 - A nucleopeptide was prepared in a convergent manner via segmental coupling of the protected biopolymers in solution. The resulting nucleopeptide (4b, 72%) containing the binding site of λ repressor and a peptide containing the consensus sequence of the DNA binding helix of the helix turn-helix-proteins was obtained using only five equivalents of the peptide relative to the oligonucleotide. This demonstrates that the recently developed method for the solution phase coupling of protected oligonucleotides is amenable to the convergent synthesis of larger nucleopeptides that are potentially capable of adopting secondary structure.

AB - A nucleopeptide was prepared in a convergent manner via segmental coupling of the protected biopolymers in solution. The resulting nucleopeptide (4b, 72%) containing the binding site of λ repressor and a peptide containing the consensus sequence of the DNA binding helix of the helix turn-helix-proteins was obtained using only five equivalents of the peptide relative to the oligonucleotide. This demonstrates that the recently developed method for the solution phase coupling of protected oligonucleotides is amenable to the convergent synthesis of larger nucleopeptides that are potentially capable of adopting secondary structure.

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Convergent solution-phase synthesis of a nucleopeptide using a protected oligonucleotide

Abstract

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