Isolation and characterization of actinoramides A-C, highly modified peptides from a marine Streptomyces sp.

Sang Jip Nam; Christopher A. Kauffman; Paul R. Jensen; William Fenical

doi:10.1016/j.tet.2011.04.051

Isolation and characterization of actinoramides A-C, highly modified peptides from a marine Streptomyces sp.

Sang Jip Nam, Christopher A. Kauffman, Paul R. Jensen, William Fenical

Department of Chemistry & Nanoscience

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

34 Scopus citations

Abstract

Reported herein is the isolation and structure elucidation of three highly modified peptides, actinoramides A-C (1-3), which are produced by a marine bacterium closely related to the genus Streptomyces. The planar structures of the actinoramides, which are composed of the unusual amino acids 2-amino-4-ureidobutanoic acid and 4-amino-3-hydroxy-2-methyl-5-phenylpentanoic acid, were assigned by chemical transformations and by interpretation of spectroscopic data, while the absolute configuration of these new peptides were defined by application of the advanced Marfey's and Mosher's methods.

Original language	English
Pages (from-to)	6707-6712
Number of pages	6
Journal	Tetrahedron
Volume	67
Issue number	35
DOIs	https://doi.org/10.1016/j.tet.2011.04.051
State	Published - 2 Sep 2011

Bibliographical note

Funding Information:
Financial support was provided by the National Cancer Institute , NIH (under grant CA044848 ). We thank Dr. C.C. Hughes for his generous advice in the determination of stereochemistry of the actinoramides. We also thank Dr. D.-C. Oh (Harvard Medical School) for providing amino acids and Prof. T. Molinski (Department of Chemistry and Biochemistry, UCSD) for providing lobocyclamide B. We especially thank Dr. K.N. Maloney for providing the information for the strain CNQ-027, and Dr. J. Pezzuto (University of Hawaii, Hilo) for providing NF-κB and aromatase bioassay data.

Keywords

Advanced Marfey's method
Advanced Mosher's method
Marine Streptomyces
Peptide hydrolysis
Unusual amino acids

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.tet.2011.04.051

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title = "Isolation and characterization of actinoramides A-C, highly modified peptides from a marine Streptomyces sp.",

abstract = "Reported herein is the isolation and structure elucidation of three highly modified peptides, actinoramides A-C (1-3), which are produced by a marine bacterium closely related to the genus Streptomyces. The planar structures of the actinoramides, which are composed of the unusual amino acids 2-amino-4-ureidobutanoic acid and 4-amino-3-hydroxy-2-methyl-5-phenylpentanoic acid, were assigned by chemical transformations and by interpretation of spectroscopic data, while the absolute configuration of these new peptides were defined by application of the advanced Marfey's and Mosher's methods.",

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author = "Nam, {Sang Jip} and Kauffman, {Christopher A.} and Jensen, {Paul R.} and William Fenical",

note = "Funding Information: Financial support was provided by the National Cancer Institute , NIH (under grant CA044848 ). We thank Dr. C.C. Hughes for his generous advice in the determination of stereochemistry of the actinoramides. We also thank Dr. D.-C. Oh (Harvard Medical School) for providing amino acids and Prof. T. Molinski (Department of Chemistry and Biochemistry, UCSD) for providing lobocyclamide B. We especially thank Dr. K.N. Maloney for providing the information for the strain CNQ-027, and Dr. J. Pezzuto (University of Hawaii, Hilo) for providing NF-κB and aromatase bioassay data. ",

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AU - Nam, Sang Jip

AU - Kauffman, Christopher A.

AU - Jensen, Paul R.

AU - Fenical, William

N1 - Funding Information: Financial support was provided by the National Cancer Institute , NIH (under grant CA044848 ). We thank Dr. C.C. Hughes for his generous advice in the determination of stereochemistry of the actinoramides. We also thank Dr. D.-C. Oh (Harvard Medical School) for providing amino acids and Prof. T. Molinski (Department of Chemistry and Biochemistry, UCSD) for providing lobocyclamide B. We especially thank Dr. K.N. Maloney for providing the information for the strain CNQ-027, and Dr. J. Pezzuto (University of Hawaii, Hilo) for providing NF-κB and aromatase bioassay data.

PY - 2011/9/2

Y1 - 2011/9/2

N2 - Reported herein is the isolation and structure elucidation of three highly modified peptides, actinoramides A-C (1-3), which are produced by a marine bacterium closely related to the genus Streptomyces. The planar structures of the actinoramides, which are composed of the unusual amino acids 2-amino-4-ureidobutanoic acid and 4-amino-3-hydroxy-2-methyl-5-phenylpentanoic acid, were assigned by chemical transformations and by interpretation of spectroscopic data, while the absolute configuration of these new peptides were defined by application of the advanced Marfey's and Mosher's methods.

AB - Reported herein is the isolation and structure elucidation of three highly modified peptides, actinoramides A-C (1-3), which are produced by a marine bacterium closely related to the genus Streptomyces. The planar structures of the actinoramides, which are composed of the unusual amino acids 2-amino-4-ureidobutanoic acid and 4-amino-3-hydroxy-2-methyl-5-phenylpentanoic acid, were assigned by chemical transformations and by interpretation of spectroscopic data, while the absolute configuration of these new peptides were defined by application of the advanced Marfey's and Mosher's methods.

KW - Advanced Marfey's method

KW - Advanced Mosher's method

KW - Marine Streptomyces

KW - Peptide hydrolysis

KW - Unusual amino acids

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JF - Tetrahedron

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ER -

Isolation and characterization of actinoramides A-C, highly modified peptides from a marine Streptomyces sp.

Abstract

Bibliographical note

Keywords

UN SDGs

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