Proof for the biosynthetic conversion of L-[Indole-15N]Tryptophan to [10-15N]Anthramycin using (13C, 15N) labelling in conjunction with 13C-NMR and mass spectral analysis

J. M. Ostrander; L. H. Hurley; A. Gavin McInnes; D. G. Smith; Jeffrey L. Wright; John A. Walter

doi:10.7164/antibiotics.33.1167

Proof for the biosynthetic conversion of L-[Indole-¹⁵N]Tryptophan to [10^-15N]Anthramycin using (¹³C, ¹⁵N) labelling in conjunction with ¹³C-NMR and mass spectral analysis

J. M. Ostrander, L. H. Hurley, A. Gavin McInnes, D. G. Smith, Jeffrey L. Wright, John A. Walter

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

8 Scopus citations

Abstract

Using ¹³C-NMR and mass spectral analysis we have demonstrated that the N-10 nitrogen of anthramycin is biosynthetically derived from the indole-nitrogen of tryptophan. Our experimental approach was to bring a ¹⁶N atom, which is derived from L-[indole-¹⁵N]tryptophan, and a ¹³C atom which is derived from DL-[l-¹³C]tyrosine, into adjacent positions of anthramycin. From resonance intensities and ¹³C-¹⁶N spin-spin coupling in the ¹³C-NMR spectrum of didehydroanhydroanthramycin, a derivative of anthramycin, we could then determine the ¹³C enrichment at C-11 and the proportion of ¹³C bonded to ¹⁶N at N-10. These results when combined with mass spectral analysis and isotopic dilution measurements proved that the indole nitrogen of tryptophan was completely retained at N-10 of anthramycin.

Original language	English (US)
Pages (from-to)	1167-1171
Number of pages	5
Journal	The Journal of Antibiotics
Volume	33
Issue number	10
DOIs	https://doi.org/10.7164/antibiotics.33.1167
State	Published - 1980
Externally published	Yes

ASJC Scopus subject areas

Pharmacology
Drug Discovery

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title = "Proof for the biosynthetic conversion of L-[Indole-15N]Tryptophan to [10-15N]Anthramycin using (13C, 15N) labelling in conjunction with 13C-NMR and mass spectral analysis",

abstract = "Using 13C-NMR and mass spectral analysis we have demonstrated that the N-10 nitrogen of anthramycin is biosynthetically derived from the indole-nitrogen of tryptophan. Our experimental approach was to bring a 16N atom, which is derived from L-[indole-15N]tryptophan, and a 13C atom which is derived from DL-[l-13C]tyrosine, into adjacent positions of anthramycin. From resonance intensities and 13C-16N spin-spin coupling in the 13C-NMR spectrum of didehydroanhydroanthramycin, a derivative of anthramycin, we could then determine the 13C enrichment at C-11 and the proportion of 13C bonded to 16N at N-10. These results when combined with mass spectral analysis and isotopic dilution measurements proved that the indole nitrogen of tryptophan was completely retained at N-10 of anthramycin.",

author = "Ostrander, {J. M.} and Hurley, {L. H.} and McInnes, {A. Gavin} and Smith, {D. G.} and Wright, {Jeffrey L.} and Walter, {John A.}",

year = "1980",

doi = "10.7164/antibiotics.33.1167",

language = "English (US)",

volume = "33",

pages = "1167--1171",

journal = "The Journal of Antibiotics",

issn = "0021-8820",

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number = "10",

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TY - JOUR

T1 - Proof for the biosynthetic conversion of L-[Indole-15N]Tryptophan to [10-15N]Anthramycin using (13C, 15N) labelling in conjunction with 13C-NMR and mass spectral analysis

AU - Ostrander, J. M.

AU - Hurley, L. H.

AU - McInnes, A. Gavin

AU - Smith, D. G.

AU - Wright, Jeffrey L.

AU - Walter, John A.

PY - 1980

Y1 - 1980

N2 - Using 13C-NMR and mass spectral analysis we have demonstrated that the N-10 nitrogen of anthramycin is biosynthetically derived from the indole-nitrogen of tryptophan. Our experimental approach was to bring a 16N atom, which is derived from L-[indole-15N]tryptophan, and a 13C atom which is derived from DL-[l-13C]tyrosine, into adjacent positions of anthramycin. From resonance intensities and 13C-16N spin-spin coupling in the 13C-NMR spectrum of didehydroanhydroanthramycin, a derivative of anthramycin, we could then determine the 13C enrichment at C-11 and the proportion of 13C bonded to 16N at N-10. These results when combined with mass spectral analysis and isotopic dilution measurements proved that the indole nitrogen of tryptophan was completely retained at N-10 of anthramycin.

AB - Using 13C-NMR and mass spectral analysis we have demonstrated that the N-10 nitrogen of anthramycin is biosynthetically derived from the indole-nitrogen of tryptophan. Our experimental approach was to bring a 16N atom, which is derived from L-[indole-15N]tryptophan, and a 13C atom which is derived from DL-[l-13C]tyrosine, into adjacent positions of anthramycin. From resonance intensities and 13C-16N spin-spin coupling in the 13C-NMR spectrum of didehydroanhydroanthramycin, a derivative of anthramycin, we could then determine the 13C enrichment at C-11 and the proportion of 13C bonded to 16N at N-10. These results when combined with mass spectral analysis and isotopic dilution measurements proved that the indole nitrogen of tryptophan was completely retained at N-10 of anthramycin.

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JO - The Journal of Antibiotics

JF - The Journal of Antibiotics

IS - 10

ER -

Proof for the biosynthetic conversion of L-[Indole-¹⁵N]Tryptophan to [10^-15N]Anthramycin using (¹³C, ¹⁵N) labelling in conjunction with ¹³C-NMR and mass spectral analysis

Abstract

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