Biosynthesis of indoleisopropionic acid by Claviceps. Biological C-methylation involving an intact methyl group

U. Hornemann; M. K. Speedie; K. M. Kelley; L. H. Hurley; H. G. Floss

doi:10.1016/0003-9861(69)90415-9

Biosynthesis of indoleisopropionic acid by Claviceps. Biological C-methylation involving an intact methyl group

U. Hornemann, M. K. Speedie, K. M. Kelley, L. H. Hurley, H. G. Floss

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Abstract

(R)-Indoleisopropionic acid (I) [(2R)-(3-indolyl)-propionic acid], a metabolite of a Claviceps strain, is formed from l-tryptophan and the intact methyl group of l-methionine. Indoleacetic acid is not incorporated into indoleisopropionic acid. (2R,S), (3S,R)-3-methyltryptophan (β-methyltryptophan, isomer B) was efficiently incorporated, but no evidence for its formation by the organism could be obtained. A hypothetical scheme for the biosynthesis of indoleisopropionic acid is presented.

Original language	English (US)
Pages (from-to)	430-440
Number of pages	11
Journal	Archives of Biochemistry and Biophysics
Volume	131
Issue number	2
DOIs	https://doi.org/10.1016/0003-9861(69)90415-9
State	Published - May 1969
Externally published	Yes

Bibliographical note

Funding Information:
1 Supported by National Institutes Grants NB 07646 and FR 05586. 2 NSF Undergraduate Summer Research ticipant, 1968.

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title = "Biosynthesis of indoleisopropionic acid by Claviceps. Biological C-methylation involving an intact methyl group",

abstract = "(R)-Indoleisopropionic acid (I) [(2R)-(3-indolyl)-propionic acid], a metabolite of a Claviceps strain, is formed from l-tryptophan and the intact methyl group of l-methionine. Indoleacetic acid is not incorporated into indoleisopropionic acid. (2R,S), (3S,R)-3-methyltryptophan (β-methyltryptophan, isomer B) was efficiently incorporated, but no evidence for its formation by the organism could be obtained. A hypothetical scheme for the biosynthesis of indoleisopropionic acid is presented.",

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note = "Funding Information: 1 Supported by National Institutes Grants NB 07646 and FR 05586. 2 NSF Undergraduate Summer Research ticipant, 1968.",

year = "1969",

month = may,

doi = "10.1016/0003-9861(69)90415-9",

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T1 - Biosynthesis of indoleisopropionic acid by Claviceps. Biological C-methylation involving an intact methyl group

AU - Hornemann, U.

AU - Speedie, M. K.

AU - Kelley, K. M.

AU - Hurley, L. H.

AU - Floss, H. G.

N1 - Funding Information: 1 Supported by National Institutes Grants NB 07646 and FR 05586. 2 NSF Undergraduate Summer Research ticipant, 1968.

PY - 1969/5

Y1 - 1969/5

N2 - (R)-Indoleisopropionic acid (I) [(2R)-(3-indolyl)-propionic acid], a metabolite of a Claviceps strain, is formed from l-tryptophan and the intact methyl group of l-methionine. Indoleacetic acid is not incorporated into indoleisopropionic acid. (2R,S), (3S,R)-3-methyltryptophan (β-methyltryptophan, isomer B) was efficiently incorporated, but no evidence for its formation by the organism could be obtained. A hypothetical scheme for the biosynthesis of indoleisopropionic acid is presented.

AB - (R)-Indoleisopropionic acid (I) [(2R)-(3-indolyl)-propionic acid], a metabolite of a Claviceps strain, is formed from l-tryptophan and the intact methyl group of l-methionine. Indoleacetic acid is not incorporated into indoleisopropionic acid. (2R,S), (3S,R)-3-methyltryptophan (β-methyltryptophan, isomer B) was efficiently incorporated, but no evidence for its formation by the organism could be obtained. A hypothetical scheme for the biosynthesis of indoleisopropionic acid is presented.

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Biosynthesis of indoleisopropionic acid by Claviceps. Biological C-methylation involving an intact methyl group

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