Totopotensamides, polyketide-cyclic peptide hybrids from a mollusk-associated bacterium Streptomyces sp.

Zhenjian Lin; Malem Flores; Imelda Forteza; Niel M. Henriksen; Gisela P. Concepcion; Gary Rosenberg; Margo G. Haygood; Baldomero M. Olivera; Alan R. Light; Thomas E. Cheatham; Eric W. Schmidt

doi:10.1021/np200886x

Totopotensamides, polyketide-cyclic peptide hybrids from a mollusk-associated bacterium Streptomyces sp.

Zhenjian Lin, Malem Flores, Imelda Forteza, Niel M. Henriksen, Gisela P. Concepcion, Gary Rosenberg, Margo G. Haygood, Baldomero M. Olivera, Alan R. Light, Thomas E. Cheatham, Eric W. Schmidt

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

27 Scopus citations

Abstract

Two new compounds, the peptide-polyketide glycoside totopotensamide A (1) and its aglycone totopotensamide B (2), were isolated from a Streptomyces sp. cultivated from the gastropod mollusk Lienardia totopotens collected in the Philippines. The compounds contain a previously undescribed polyketide component, a novel 2,3-diaminobutyric acid-containing macrolactam, and a new amino acid, 4-chloro-5,7-dihydroxy-6-methylphenylglycine. The application of Marfey's method to phenylglycine derivatives was explored using quantum mechanical calculations and NMR.

Original language	English (US)
Pages (from-to)	644-649
Number of pages	6
Journal	Journal of Natural Products
Volume	75
Issue number	4
DOIs	https://doi.org/10.1021/np200886x
State	Published - Apr 27 2012
Externally published	Yes

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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10.1021/np200886x

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title = "Totopotensamides, polyketide-cyclic peptide hybrids from a mollusk-associated bacterium Streptomyces sp.",

abstract = "Two new compounds, the peptide-polyketide glycoside totopotensamide A (1) and its aglycone totopotensamide B (2), were isolated from a Streptomyces sp. cultivated from the gastropod mollusk Lienardia totopotens collected in the Philippines. The compounds contain a previously undescribed polyketide component, a novel 2,3-diaminobutyric acid-containing macrolactam, and a new amino acid, 4-chloro-5,7-dihydroxy-6-methylphenylglycine. The application of Marfey's method to phenylglycine derivatives was explored using quantum mechanical calculations and NMR.",

author = "Zhenjian Lin and Malem Flores and Imelda Forteza and Henriksen, {Niel M.} and Concepcion, {Gisela P.} and Gary Rosenberg and Haygood, {Margo G.} and Olivera, {Baldomero M.} and Light, {Alan R.} and Cheatham, {Thomas E.} and Schmidt, {Eric W.}",

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doi = "10.1021/np200886x",

language = "English (US)",

volume = "75",

pages = "644--649",

journal = "Journal of Natural Products",

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TY - JOUR

T1 - Totopotensamides, polyketide-cyclic peptide hybrids from a mollusk-associated bacterium Streptomyces sp.

AU - Lin, Zhenjian

AU - Flores, Malem

AU - Forteza, Imelda

AU - Henriksen, Niel M.

AU - Concepcion, Gisela P.

AU - Rosenberg, Gary

AU - Haygood, Margo G.

AU - Olivera, Baldomero M.

AU - Light, Alan R.

AU - Cheatham, Thomas E.

AU - Schmidt, Eric W.

PY - 2012/4/27

Y1 - 2012/4/27

N2 - Two new compounds, the peptide-polyketide glycoside totopotensamide A (1) and its aglycone totopotensamide B (2), were isolated from a Streptomyces sp. cultivated from the gastropod mollusk Lienardia totopotens collected in the Philippines. The compounds contain a previously undescribed polyketide component, a novel 2,3-diaminobutyric acid-containing macrolactam, and a new amino acid, 4-chloro-5,7-dihydroxy-6-methylphenylglycine. The application of Marfey's method to phenylglycine derivatives was explored using quantum mechanical calculations and NMR.

AB - Two new compounds, the peptide-polyketide glycoside totopotensamide A (1) and its aglycone totopotensamide B (2), were isolated from a Streptomyces sp. cultivated from the gastropod mollusk Lienardia totopotens collected in the Philippines. The compounds contain a previously undescribed polyketide component, a novel 2,3-diaminobutyric acid-containing macrolactam, and a new amino acid, 4-chloro-5,7-dihydroxy-6-methylphenylglycine. The application of Marfey's method to phenylglycine derivatives was explored using quantum mechanical calculations and NMR.

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Totopotensamides, polyketide-cyclic peptide hybrids from a mollusk-associated bacterium Streptomyces sp.

Abstract

ASJC Scopus subject areas

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