Efficient one-pot cyclization/folding of Rhesus θ-defensin-1 (RTD-1)

Teshome L. Aboye; Yilong Li; Subhabrata Majumder; Jinfeng Hao; Alexander Shekhtman; Julio A. Camarero

doi:10.1016/j.bmcl.2012.02.080

Efficient one-pot cyclization/folding of Rhesus θ-defensin-1 (RTD-1)

Teshome L. Aboye, Yilong Li, Subhabrata Majumder, Jinfeng Hao, Alexander Shekhtman, Julio A. Camarero

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

26 Scopus citations

Abstract

We report an efficient approach for the chemical synthesis of Rhesus θ-defensin-1 (RTD-1) using Fmoc-based solid-phase peptide synthesis in combination with an intramolecular version of native chemical ligation. The corresponding linear thioester precursor was cyclized and folded in a one-pot reaction using reduced glutathione. The reaction was extremely efficiently yielding natively folded RTD-1 with minimal or no purification at all. This approach is fully compatible with the high throughput production of chemical libraries using this peptide scaffold.

Original language	English (US)
Pages (from-to)	2823-2826
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	22
Issue number	8
DOIs	https://doi.org/10.1016/j.bmcl.2012.02.080
State	Published - Apr 15 2012
Externally published	Yes

Bibliographical note

Funding Information:
This work was supported by National Institutes of Health Research Grant R01-GM090323 (J.A.C.) and NIH Grant 5R01GM085006-02 (A.S.); and by the Department of Defense Congressionally Directed Medical Research Program Grant PC09305 (J.A.C.).

Keywords

Antimicrobial peptide
Cyclic peptide
Defensin

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abstract = "We report an efficient approach for the chemical synthesis of Rhesus θ-defensin-1 (RTD-1) using Fmoc-based solid-phase peptide synthesis in combination with an intramolecular version of native chemical ligation. The corresponding linear thioester precursor was cyclized and folded in a one-pot reaction using reduced glutathione. The reaction was extremely efficiently yielding natively folded RTD-1 with minimal or no purification at all. This approach is fully compatible with the high throughput production of chemical libraries using this peptide scaffold.",

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AU - Li, Yilong

AU - Majumder, Subhabrata

AU - Hao, Jinfeng

AU - Shekhtman, Alexander

AU - Camarero, Julio A.

N1 - Funding Information: This work was supported by National Institutes of Health Research Grant R01-GM090323 (J.A.C.) and NIH Grant 5R01GM085006-02 (A.S.); and by the Department of Defense Congressionally Directed Medical Research Program Grant PC09305 (J.A.C.).

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KW - Cyclic peptide

KW - Defensin

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Efficient one-pot cyclization/folding of Rhesus θ-defensin-1 (RTD-1)

Abstract

Bibliographical note

Keywords

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