Mirabimides A-D, new N-acylpyrrolinones from the blue-green alga Scytonema mirabile

Shmuel Carmeli; Richard E. Moore; Gregory M.L. Patterson

doi:10.1016/S0040-4020(01)96119-8

Mirabimides A-D, new N-acylpyrrolinones from the blue-green alga Scytonema mirabile

Shmuel Carmeli^*
, Richard E. Moore
, Gregory M.L. Patterson

^*Corresponding author for this work

University of Hawai'i at Mānoa

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

45 Scopus citations

Abstract

Mirabimide A, the major imide from the terrestrial blue-green alga Scytonema mirabile (Dillwyn) Bornet (strain BY-8-1), is N-[2-(N,N-dimethylleucyl)oxy-3-methylpentanoyl-N-methylvalyl-prolyl]-4-methoxy-5-isopropyl-3-pyrrolin-2-one. Mirabimides B-D are the valyl, 2-oxy-3-methylbutanoyl, and N-acetyl-N-methylleucyl analogs, respectively. The absolute configurations of the five asymmetric carbons in the mirabimides are proposed to be all S, but the assignments for the dimethylleucine units in A-C and the hydroxyacid units in B-D are tentative.

Original language	English
Pages (from-to)	2087-2096
Number of pages	10
Journal	Tetrahedron
Volume	47
Issue number	12-13
DOIs	https://doi.org/10.1016/S0040-4020(01)96119-8
State	Published - 1991
Externally published	Yes

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title = "Mirabimides A-D, new N-acylpyrrolinones from the blue-green alga Scytonema mirabile",

abstract = "Mirabimide A, the major imide from the terrestrial blue-green alga Scytonema mirabile (Dillwyn) Bornet (strain BY-8-1), is N-[2-(N,N-dimethylleucyl)oxy-3-methylpentanoyl-N-methylvalyl-prolyl]-4-methoxy-5-isopropyl-3-pyrrolin-2-one. Mirabimides B-D are the valyl, 2-oxy-3-methylbutanoyl, and N-acetyl-N-methylleucyl analogs, respectively. The absolute configurations of the five asymmetric carbons in the mirabimides are proposed to be all S, but the assignments for the dimethylleucine units in A-C and the hydroxyacid units in B-D are tentative.",

author = "Shmuel Carmeli and Moore, \{Richard E.\} and Patterson, \{Gregory M.L.\}",

year = "1991",

doi = "10.1016/S0040-4020(01)96119-8",

language = "אנגלית",

volume = "47",

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number = "12-13",

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T1 - Mirabimides A-D, new N-acylpyrrolinones from the blue-green alga Scytonema mirabile

AU - Carmeli, Shmuel

AU - Moore, Richard E.

AU - Patterson, Gregory M.L.

PY - 1991

Y1 - 1991

N2 - Mirabimide A, the major imide from the terrestrial blue-green alga Scytonema mirabile (Dillwyn) Bornet (strain BY-8-1), is N-[2-(N,N-dimethylleucyl)oxy-3-methylpentanoyl-N-methylvalyl-prolyl]-4-methoxy-5-isopropyl-3-pyrrolin-2-one. Mirabimides B-D are the valyl, 2-oxy-3-methylbutanoyl, and N-acetyl-N-methylleucyl analogs, respectively. The absolute configurations of the five asymmetric carbons in the mirabimides are proposed to be all S, but the assignments for the dimethylleucine units in A-C and the hydroxyacid units in B-D are tentative.

AB - Mirabimide A, the major imide from the terrestrial blue-green alga Scytonema mirabile (Dillwyn) Bornet (strain BY-8-1), is N-[2-(N,N-dimethylleucyl)oxy-3-methylpentanoyl-N-methylvalyl-prolyl]-4-methoxy-5-isopropyl-3-pyrrolin-2-one. Mirabimides B-D are the valyl, 2-oxy-3-methylbutanoyl, and N-acetyl-N-methylleucyl analogs, respectively. The absolute configurations of the five asymmetric carbons in the mirabimides are proposed to be all S, but the assignments for the dimethylleucine units in A-C and the hydroxyacid units in B-D are tentative.

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JO - Tetrahedron

JF - Tetrahedron

IS - 12-13

ER -

Mirabimides A-D, new N-acylpyrrolinones from the blue-green alga Scytonema mirabile

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