Clavicipitic Acid: Its Structure, Biosynthesis, and Role in Ergot Alkaloid Formation

James E. Robbers; Hideaki Otsuka; Heinz G. Floss; Edward V. Arnold; Jon Clardy

doi:10.1021/jo01294a039

Clavicipitic Acid: Its Structure, Biosynthesis, and Role in Ergot Alkaloid Formation

James E. Robbers, Hideaki Otsuka, Heinz G. Floss, Edward V. Arnold, Jon Clardy

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Abstract

Clavicipitic acid, a metabolite of Claviceps strain SD 58, is a mixture of isomers, the major one of which was shown by a single-crystal X-ray analysis to give structure Ha. It is formed from tryptophan and mevalonic acid but is not further converted into the tetracyclic ergot alkaloid elymoclavine. Its formation represents a derailment of ergoline biosynthesis after the first pathway-specific step, the isoprenylation of tryptophan.

Original language	English (US)
Pages (from-to)	1117-1121
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	45
Issue number	6
DOIs	https://doi.org/10.1021/jo01294a039
State	Published - Mar 1980
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo01294a039

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title = "Clavicipitic Acid: Its Structure, Biosynthesis, and Role in Ergot Alkaloid Formation",

abstract = "Clavicipitic acid, a metabolite of Claviceps strain SD 58, is a mixture of isomers, the major one of which was shown by a single-crystal X-ray analysis to give structure Ha. It is formed from tryptophan and mevalonic acid but is not further converted into the tetracyclic ergot alkaloid elymoclavine. Its formation represents a derailment of ergoline biosynthesis after the first pathway-specific step, the isoprenylation of tryptophan.",

author = "Robbers, {James E.} and Hideaki Otsuka and Floss, {Heinz G.} and Arnold, {Edward V.} and Jon Clardy",

year = "1980",

month = mar,

doi = "10.1021/jo01294a039",

language = "English (US)",

volume = "45",

pages = "1117--1121",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

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T1 - Clavicipitic Acid

T2 - Its Structure, Biosynthesis, and Role in Ergot Alkaloid Formation

AU - Robbers, James E.

AU - Otsuka, Hideaki

AU - Floss, Heinz G.

AU - Arnold, Edward V.

AU - Clardy, Jon

PY - 1980/3

Y1 - 1980/3

N2 - Clavicipitic acid, a metabolite of Claviceps strain SD 58, is a mixture of isomers, the major one of which was shown by a single-crystal X-ray analysis to give structure Ha. It is formed from tryptophan and mevalonic acid but is not further converted into the tetracyclic ergot alkaloid elymoclavine. Its formation represents a derailment of ergoline biosynthesis after the first pathway-specific step, the isoprenylation of tryptophan.

AB - Clavicipitic acid, a metabolite of Claviceps strain SD 58, is a mixture of isomers, the major one of which was shown by a single-crystal X-ray analysis to give structure Ha. It is formed from tryptophan and mevalonic acid but is not further converted into the tetracyclic ergot alkaloid elymoclavine. Its formation represents a derailment of ergoline biosynthesis after the first pathway-specific step, the isoprenylation of tryptophan.

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 6

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Clavicipitic Acid: Its Structure, Biosynthesis, and Role in Ergot Alkaloid Formation

Abstract

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