Stereochemistry of the methyne-methylene conversion in the biogeneration of (S)-δ-decanolide and (S)-γ-dodecanolide from (13RS)-13- hydroxyoctadeca-9Z,11E-dienoic and (10RS)-10-hydroxyoctadec-8E-enoic acid

Giovanni Fronza; Claudio Fuganti; Piero Grasselli; Andrea Mele; Gianna Allegrone; Massimo Barbeni; Antonella Pisciotta

doi:10.1039/p19910002977

Stereochemistry of the methyne-methylene conversion in the biogeneration of (S)-δ-decanolide and (S)-γ-dodecanolide from (13RS)-13- hydroxyoctadeca-9Z,11E-dienoic and (10RS)-10-hydroxyoctadec-8E-enoic acid

Giovanni Fronza, Claudio Fuganti, Piero Grasselli, Andrea Mele, Gianna Allegrone, Massimo Barbeni, Antonella Pisciotta

Risultato della ricerca: Contributo su rivista › Articolo in rivista › peer review

Abstract

In Cladosporium suaveolens the bioconversion of (13RS)-13-hydroxy-[9,10,11, 12-²H₄]octadeca-9Z,11E-dienoic acid into axially, 2,3,4-trideuteriated (S)-δ-decanolide indicates that protonation of the dienic system occurring at some stage of the degradative sequence takes place on the same face of the molecule. The protonation at position 9 of (10RS)-10-hydroxy-[9,10-²H₂]octadeca-8E-enoic acid occurring in Yarrowia lipolytica during the biogeneration of (S)-γ-dodecanolide shows the same steric course.

Lingua originale	Inglese
pagine (da-a)	2977-2981
Numero di pagine	5
Rivista	Journal of the Chemical Society, Perkin Transactions 1
Numero di pubblicazione	12
DOI	https://doi.org/10.1039/p19910002977
Stato di pubblicazione	Pubblicato - 1991
Pubblicato esternamente	Sì

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10.1039/p19910002977

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Fronza, G., Fuganti, C., Grasselli, P., Mele, A., Allegrone, G., Barbeni, M., & Pisciotta, A. (1991). Stereochemistry of the methyne-methylene conversion in the biogeneration of (S)-δ-decanolide and (S)-γ-dodecanolide from (13RS)-13- hydroxyoctadeca-9Z,11E-dienoic and (10RS)-10-hydroxyoctadec-8E-enoic acid. Journal of the Chemical Society, Perkin Transactions 1, (12), 2977-2981. https://doi.org/10.1039/p19910002977

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title = "Stereochemistry of the methyne-methylene conversion in the biogeneration of (S)-δ-decanolide and (S)-γ-dodecanolide from (13RS)-13- hydroxyoctadeca-9Z,11E-dienoic and (10RS)-10-hydroxyoctadec-8E-enoic acid",

abstract = "In Cladosporium suaveolens the bioconversion of (13RS)-13-hydroxy-[9,10,11, 12-2H4]octadeca-9Z,11E-dienoic acid into axially, 2,3,4-trideuteriated (S)-δ-decanolide indicates that protonation of the dienic system occurring at some stage of the degradative sequence takes place on the same face of the molecule. The protonation at position 9 of (10RS)-10-hydroxy-[9,10-2H2]octadeca-8E-enoic acid occurring in Yarrowia lipolytica during the biogeneration of (S)-γ-dodecanolide shows the same steric course.",

author = "Giovanni Fronza and Claudio Fuganti and Piero Grasselli and Andrea Mele and Gianna Allegrone and Massimo Barbeni and Antonella Pisciotta",

year = "1991",

doi = "10.1039/p19910002977",

language = "English",

pages = "2977--2981",

journal = "Journal of the Chemical Society, Perkin Transactions 1",

issn = "1472-7781",

publisher = "Chemical Society",

number = "12",

}

Fronza, G, Fuganti, C, Grasselli, P, Mele, A, Allegrone, G, Barbeni, M & Pisciotta, A 1991, 'Stereochemistry of the methyne-methylene conversion in the biogeneration of (S)-δ-decanolide and (S)-γ-dodecanolide from (13RS)-13- hydroxyoctadeca-9Z,11E-dienoic and (10RS)-10-hydroxyoctadec-8E-enoic acid', Journal of the Chemical Society, Perkin Transactions 1, n. 12, pagg. 2977-2981. https://doi.org/10.1039/p19910002977

Stereochemistry of the methyne-methylene conversion in the biogeneration of (S)-δ-decanolide and (S)-γ-dodecanolide from (13RS)-13- hydroxyoctadeca-9Z,11E-dienoic and (10RS)-10-hydroxyoctadec-8E-enoic acid. / Fronza, Giovanni; Fuganti, Claudio; Grasselli, Piero et al.
In: Journal of the Chemical Society, Perkin Transactions 1, N. 12, 1991, pag. 2977-2981.

Risultato della ricerca: Contributo su rivista › Articolo in rivista › peer review

TY - JOUR

T1 - Stereochemistry of the methyne-methylene conversion in the biogeneration of (S)-δ-decanolide and (S)-γ-dodecanolide from (13RS)-13- hydroxyoctadeca-9Z,11E-dienoic and (10RS)-10-hydroxyoctadec-8E-enoic acid

AU - Fronza, Giovanni

AU - Fuganti, Claudio

AU - Grasselli, Piero

AU - Mele, Andrea

AU - Allegrone, Gianna

AU - Barbeni, Massimo

AU - Pisciotta, Antonella

PY - 1991

Y1 - 1991

N2 - In Cladosporium suaveolens the bioconversion of (13RS)-13-hydroxy-[9,10,11, 12-2H4]octadeca-9Z,11E-dienoic acid into axially, 2,3,4-trideuteriated (S)-δ-decanolide indicates that protonation of the dienic system occurring at some stage of the degradative sequence takes place on the same face of the molecule. The protonation at position 9 of (10RS)-10-hydroxy-[9,10-2H2]octadeca-8E-enoic acid occurring in Yarrowia lipolytica during the biogeneration of (S)-γ-dodecanolide shows the same steric course.

AB - In Cladosporium suaveolens the bioconversion of (13RS)-13-hydroxy-[9,10,11, 12-2H4]octadeca-9Z,11E-dienoic acid into axially, 2,3,4-trideuteriated (S)-δ-decanolide indicates that protonation of the dienic system occurring at some stage of the degradative sequence takes place on the same face of the molecule. The protonation at position 9 of (10RS)-10-hydroxy-[9,10-2H2]octadeca-8E-enoic acid occurring in Yarrowia lipolytica during the biogeneration of (S)-γ-dodecanolide shows the same steric course.

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U2 - 10.1039/p19910002977

DO - 10.1039/p19910002977

M3 - Article

SN - 1472-7781

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JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

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Fronza G, Fuganti C, Grasselli P, Mele A, Allegrone G, Barbeni M et al. Stereochemistry of the methyne-methylene conversion in the biogeneration of (S)-δ-decanolide and (S)-γ-dodecanolide from (13RS)-13- hydroxyoctadeca-9Z,11E-dienoic and (10RS)-10-hydroxyoctadec-8E-enoic acid. Journal of the Chemical Society, Perkin Transactions 1. 1991;(12):2977-2981. doi: 10.1039/p19910002977

Stereochemistry of the methyne-methylene conversion in the biogeneration of (S)-δ-decanolide and (S)-γ-dodecanolide from (13RS)-13- hydroxyoctadeca-9Z,11E-dienoic and (10RS)-10-hydroxyoctadec-8E-enoic acid

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