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

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

7 Scopus citations

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

ASJC Scopus subject areas

Biophysics
Biochemistry
Molecular Biology

Access to Document

10.1016/0003-9861(69)90415-9

Cite this

@article{5357621914a34deb8fea7961a1cfe963,

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.",

author = "U. Hornemann and Speedie, \{M. K.\} and Kelley, \{K. M.\} and Hurley, \{L. H.\} and Floss, \{H. G.\}",

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",

language = "English (US)",

volume = "131",

pages = "430--440",

journal = "Archives of Biochemistry and Biophysics",

issn = "0003-9861",

publisher = "Academic Press Inc.",

number = "2",

}

TY - JOUR

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.

UR - https://www.scopus.com/pages/publications/0014510835

UR - https://www.scopus.com/pages/publications/0014510835#tab=citedBy

U2 - 10.1016/0003-9861(69)90415-9

DO - 10.1016/0003-9861(69)90415-9

M3 - Article

C2 - 5787216

AN - SCOPUS:0014510835

SN - 0003-9861

VL - 131

SP - 430

EP - 440

JO - Archives of Biochemistry and Biophysics

JF - Archives of Biochemistry and Biophysics

IS - 2

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this