Stereochemistry of the decarboxylation of l-ornithine with ornithine decarboxylase from mouse kidney

Gary R. Orr; Steven J. Gould; Anthony E. Pegg; James E. Seely; James K. Coward

doi:10.1016/0045-2068(84)90009-9

Stereochemistry of the decarboxylation of l-ornithine with ornithine decarboxylase from mouse kidney

Gary R. Orr, Steven J. Gould, Anthony E. Pegg, James E. Seely, James K. Coward

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

8 Scopus citations

Abstract

Using highly purified ornithine decarboxylase isolated from androgen-treated mice, [1R-²H]putrescine was generated by the decarboxylation of l-ornithine in D₂O, and [1S-²H]putrescine was generated from [2-²H]ornithine by carrying out the decarboxylation in H₂O. Chirality of the putrescines was then determined from the 200-MHz ¹H NMR spectra of their bis-camphanamides in the presence of Eu(fod)₃. These results demonstrated that decarboxylation had taken place with retention of configuration.

Original language	English (US)
Pages (from-to)	252-258
Number of pages	7
Journal	Bioorganic Chemistry
Volume	12
Issue number	3
DOIs	https://doi.org/10.1016/0045-2068(84)90009-9
State	Published - Sep 1984

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Biology
Drug Discovery
Organic Chemistry

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@article{aa2cdf48ef754795a4374ff7a44ec468,

title = "Stereochemistry of the decarboxylation of l-ornithine with ornithine decarboxylase from mouse kidney",

abstract = "Using highly purified ornithine decarboxylase isolated from androgen-treated mice, [1R-2H]putrescine was generated by the decarboxylation of l-ornithine in D2O, and [1S-2H]putrescine was generated from [2-2H]ornithine by carrying out the decarboxylation in H2O. Chirality of the putrescines was then determined from the 200-MHz 1H NMR spectra of their bis-camphanamides in the presence of Eu(fod)3. These results demonstrated that decarboxylation had taken place with retention of configuration.",

author = "Orr, {Gary R.} and Gould, {Steven J.} and Pegg, {Anthony E.} and Seely, {James E.} and Coward, {James K.}",

note = "Funding Information: This work was supported by grants to S.J.G. (GM32102), to A.E.P. (CA-18138) and to J.K.C. (GM30286) from the U.S. Public Health Service; J.E.S. is recipient of a training fellowship (IT32 HL-07223). NMR spectra were obtained on a Varian XL-200 FT spectrometer at RPI, and mass spectra were obtained on a MATCH-7 spectrometer at OSU. Mr. Rodger Kohnert is thanked for obtaining the mass spectra.",

year = "1984",

month = sep,

doi = "10.1016/0045-2068(84)90009-9",

language = "English (US)",

volume = "12",

pages = "252--258",

journal = "Bioorganic Chemistry",

issn = "0045-2068",

publisher = "Academic Press Inc.",

number = "3",

}

TY - JOUR

T1 - Stereochemistry of the decarboxylation of l-ornithine with ornithine decarboxylase from mouse kidney

AU - Orr, Gary R.

AU - Gould, Steven J.

AU - Pegg, Anthony E.

AU - Seely, James E.

AU - Coward, James K.

N1 - Funding Information: This work was supported by grants to S.J.G. (GM32102), to A.E.P. (CA-18138) and to J.K.C. (GM30286) from the U.S. Public Health Service; J.E.S. is recipient of a training fellowship (IT32 HL-07223). NMR spectra were obtained on a Varian XL-200 FT spectrometer at RPI, and mass spectra were obtained on a MATCH-7 spectrometer at OSU. Mr. Rodger Kohnert is thanked for obtaining the mass spectra.

PY - 1984/9

Y1 - 1984/9

N2 - Using highly purified ornithine decarboxylase isolated from androgen-treated mice, [1R-2H]putrescine was generated by the decarboxylation of l-ornithine in D2O, and [1S-2H]putrescine was generated from [2-2H]ornithine by carrying out the decarboxylation in H2O. Chirality of the putrescines was then determined from the 200-MHz 1H NMR spectra of their bis-camphanamides in the presence of Eu(fod)3. These results demonstrated that decarboxylation had taken place with retention of configuration.

AB - Using highly purified ornithine decarboxylase isolated from androgen-treated mice, [1R-2H]putrescine was generated by the decarboxylation of l-ornithine in D2O, and [1S-2H]putrescine was generated from [2-2H]ornithine by carrying out the decarboxylation in H2O. Chirality of the putrescines was then determined from the 200-MHz 1H NMR spectra of their bis-camphanamides in the presence of Eu(fod)3. These results demonstrated that decarboxylation had taken place with retention of configuration.

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SN - 0045-2068

VL - 12

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EP - 258

JO - Bioorganic Chemistry

JF - Bioorganic Chemistry

IS - 3

ER -

Stereochemistry of the decarboxylation of l-ornithine with ornithine decarboxylase from mouse kidney

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