Stereospecific syntheses of both diastereomers of (.+-.)-2-amino-4-methyl-5-hexenoic acid

Snider, Barry B.; Duncia, John V.

doi:10.1021/jo00329a015

Cited by 10 publications

(3 citation statements)

References 2 publications

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“…By contrast, the transition state (T10) leading to the observed product has no significant steric interactions. 129 stituted alkenes also shows a preference for hydrogen transfer from the alkyl group cis to the alkenyl hydrogen.…”

Section: B Regloselectlonmentioning

confidence: 99%

Asymmetric ene reactions in organic synthesis

Mikami¹,

Shimizu²

1992

Chem. Rev.

613

184

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Section: B Regloselectlonmentioning

confidence: 99%

Asymmetric ene reactions in organic synthesis

Mikami¹,

Shimizu²

1992

Chem. Rev.

613

184

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“…UC5159) (Kelly et al 1969) and 2S-(-)-2-amino-4-methyl-5-hexenoic acid from Boletus, section Ixocomus, group Nudi (Rudzats et al 1972;Gellert et al 1973), were isolated. Rudzats et al reported the absolute stereochemistry was 2S,4S (Gellert et al 1978); however, Snider and Dunčia corrected the stereochemistry to 2S,4R and determined 2S-(+)-2-amino-4-methyl-5-hexenoic acid as 2S,4S stereochemistry (Snider & Dunčia 1981). There are two symmetric carbons in 1, and the relative stereochemistry was determined by comparison of 1 H-NMR in D 2 O with synthesized diastereomers pairs (racemic mixtures) (Snider & Dunčia 1981).…”

Section: Resultsmentioning

confidence: 99%

“…Rudzats et al reported the absolute stereochemistry was 2S,4S (Gellert et al 1978); however, Snider and Dunčia corrected the stereochemistry to 2S,4R and determined 2S-(+)-2-amino-4-methyl-5-hexenoic acid as 2S,4S stereochemistry (Snider & Dunčia 1981). There are two symmetric carbons in 1, and the relative stereochemistry was determined by comparison of 1 H-NMR in D 2 O with synthesized diastereomers pairs (racemic mixtures) (Snider & Dunčia 1981). The data of 1 were in accordance with a 2R*,4S* isomer.…”

Section: Resultsmentioning

confidence: 99%

Isolation of (2S,4R)-2-amino-4-methyl-hex-5-enoic acid, a nonprotein amino acid, as an allelochemical from the fruiting bodies of Boletus fraternus Peck.

Araya

Nagai

Otaka

2014

Journal of Plant Interactions

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The mushroom Boletus fraternus Peck. shows allelopathy and suppresses the growth of broad leaf plants in nature. According to a bioassay-guided fractionation of the fruiting body of the fungus, a rare nonprotein amino acid was isolated as a major allelochemical. The chemical structure of the compound was determined to be (2S,4R)-2-amino-4-methyl-hex-5-enoic acid (5-dehydrohomoleucine) by analysis of 1 H-and 13 C-nuclear magnetic resonance spectra and comparison with data from the literature. The allelochemical caused 50% inhibition of lettuce seedling radicle growth at a concentration of 34 ppm (w/v). Further, since radicle growth was directed away from the filter paper to prevent contact with the allelochemical at concentrations higher than 300 ppm (w/v), the fungus may use the allelochemical to protect its immediate environment from contamination by other plants.

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Neue natürliche Aminosäuren

Wagner¹,

Musso²

1983

Angewandte Chemie

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Professor Hans Brochann zum 80. Geburtstag gewidmetDie Mehnahl der ca. 500 heute bekannten natiirlichen Aminosiiuren wurde in den letzten 30 Jahren entdeckt, z. B. bei der Suche nach neuen Antibiotica in der Kulturfliissigkeit von Mikroorganismen oder als Bestandteile dieser Antibiotica, in Pilzen, in Samen, in zahlreichen Pflanzen und Frtichten, auch in Ktlrperfliissigkeiten von Tieren in gebundener Form. Etwa 240 dieser Aminosauren kommen auch frei in der Natur vor, einige nur als Zwischenprodukte des Stoffwechsels. Der vorliegende Beitrag vermittelt einen ifberblick iiber die Entwicklung dieses Gebietes seit 1956, als die letzte Zusammenfassung erschien. K u n und summarisch abgehandelt werden neue ungesiittigte Aminosauren, Cyclopropan-und Cyclobutanaminosiuren, heterocyclische Aminosauren, halogenhaltige Aminosauren, schwefel-, selen-und phosphorhaltige Aminosauren sowie aliphatische AminosBuren. Nur in wenigen Fallen, z. B. bei Betalaminsaure und Muscaflavin, wird die Biosynthese ausfiihrlich erlautert. Historkhe Einleitung

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Stereospecific syntheses of both diastereomers of (.+-.)-2-amino-4-methyl-5-hexenoic acid

Cited by 10 publications

References 2 publications

Asymmetric ene reactions in organic synthesis

Asymmetric ene reactions in organic synthesis

Isolation of (2S,4R)-2-amino-4-methyl-hex-5-enoic acid, a nonprotein amino acid, as an allelochemical from the fruiting bodies of Boletus fraternus Peck.

Neue natürliche Aminosäuren

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