共 17 条
A Tyrosine Aminomutase from Rice (Oryza sativa) lsomerizes (S)-α- to (R)-β-Tyrosine with Unique High Enantioselectivity and Retention of Configuration
被引:15
作者:

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King, Zayna
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机构:
CUNY Medgar Evers Coll, Brooklyn, NY 11225 USA Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA

Walker, Kevin D.
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Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA
Michigan State Univ, Dept Biochem & Mol Biol, E Lansing, MI 48824 USA Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA
机构:
[1] Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA
[2] Michigan State Univ, Dept Biochem & Mol Biol, E Lansing, MI 48824 USA
[3] CUNY Medgar Evers Coll, Brooklyn, NY 11225 USA
关键词:
PHENYLALANINE AMINOMUTASE;
BIOSYNTHESIS;
MECHANISM;
STEREOCHEMISTRY;
PATHWAY;
D O I:
10.1021/acs.biochem.5b01331
中图分类号:
Q5 [生物化学];
Q7 [分子生物学];
学科分类号:
071010 ;
081704 ;
摘要:
A recently discovered 3,5-dihydro-5-methylidene-4H-imidazol-4-one (MIO)-dependent tyrosine aminomutase (OsTAM) from rice [Yan, J., et al. (2015) Plant Cell 27, 1265] converts (S)-alpha-tyrosine to a mixture of (R)- and (S)-beta-tyrosines, with high (94%) enantiomeric excess, which does not change with pH, like it does for two bacterial TAMs. The K-M of 490 mu M and the k(cat) of 0.005 s(-1) are similar for other TAM enzymes. OsTAM is unique and also catalyzes (R)-beta- from (S)-alpha-phenylalanine. OsTAM principally retains the configuration at the reactive C-alpha and C-beta centers during catalysis much like the phenylalanine aminomutase on the Taxol biosynthetic pathway in Taxus plants.
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页码:1 / 4
页数:4
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共 17 条
[1]
Thermal Bifunctionality of Bacterial Phenylalanine Aminomutase and Ammonia Lyase Enzymes
[J].
Chesters, Christopher
;
Wilding, Matthew
;
Goodall, Mark
;
Micklefield, Jason
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2012, 51 (18)
:4344-4348

Chesters, Christopher
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Manchester, Sch Chem, Manchester M1 7DN, Lancs, England
Univ Manchester, Manchester Interdisciplinary Bioctr, Manchester M1 7DN, Lancs, England Univ Manchester, Sch Chem, Manchester M1 7DN, Lancs, England

论文数: 引用数:
h-index:
机构:

Goodall, Mark
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Manchester, Sch Chem, Manchester M1 7DN, Lancs, England
Univ Manchester, Manchester Interdisciplinary Bioctr, Manchester M1 7DN, Lancs, England Univ Manchester, Sch Chem, Manchester M1 7DN, Lancs, England

论文数: 引用数:
h-index:
机构:
[2]
Kinetic analysis of the 4-methylideneimidazole-5-one-containing tyrosine aminomutase in enediyne antitumor antibiotic C-1027 biosynthesis
[J].
Christenson, SD
;
Wu, WM
;
Spies, MA
;
Shen, B
;
Toney, MD
.
BIOCHEMISTRY,
2003, 42 (43)
:12708-12718

Christenson, SD
论文数: 0 引用数: 0
h-index: 0
机构: Univ Calif Davis, Dept Chem, Davis, CA 95616 USA

Wu, WM
论文数: 0 引用数: 0
h-index: 0
机构: Univ Calif Davis, Dept Chem, Davis, CA 95616 USA

Spies, MA
论文数: 0 引用数: 0
h-index: 0
机构: Univ Calif Davis, Dept Chem, Davis, CA 95616 USA

Shen, B
论文数: 0 引用数: 0
h-index: 0
机构: Univ Calif Davis, Dept Chem, Davis, CA 95616 USA

Toney, MD
论文数: 0 引用数: 0
h-index: 0
机构: Univ Calif Davis, Dept Chem, Davis, CA 95616 USA
[3]
The mechanism of MIO-based aminomutases in β-amino acid biosynthesis
[J].
Christianson, Carl V.
;
Montavon, Timothy J.
;
Festin, Grace M.
;
Cooke, Heather A.
;
Shen, Ben
;
Bruner, Steven D.
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2007, 129 (51)
:15744-+

Christianson, Carl V.
论文数: 0 引用数: 0
h-index: 0
机构:
Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA

Montavon, Timothy J.
论文数: 0 引用数: 0
h-index: 0
机构:
Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA

Festin, Grace M.
论文数: 0 引用数: 0
h-index: 0
机构:
Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA

Cooke, Heather A.
论文数: 0 引用数: 0
h-index: 0
机构:
Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA

Shen, Ben
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Wisconsin, Dept Chem, Div Pharmaceut Sci, Madison, WI 53705 USA
Univ Wisconsin, Natl Cooperat Drug Discovery Grp, Madison, WI 53705 USA Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA

Bruner, Steven D.
论文数: 0 引用数: 0
h-index: 0
机构:
Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA
[4]
The structure of L-tyrosine 2,3-aminomutase from the C-1027 enediyne antitumor antibiotic biosynthetic pathway
[J].
Christianson, Carl V.
;
Montavon, Timothy J.
;
Van Lanen, Steven G.
;
Shen, Ben
;
Bruner, Steven D.
.
BIOCHEMISTRY,
2007, 46 (24)
:7205-7214

Christianson, Carl V.
论文数: 0 引用数: 0
h-index: 0
机构: Boston Coll, Dept Chem, Eugene F Merkert Chem Ctr, Chestnut Hill, MA 02467 USA

Montavon, Timothy J.
论文数: 0 引用数: 0
h-index: 0
机构: Boston Coll, Dept Chem, Eugene F Merkert Chem Ctr, Chestnut Hill, MA 02467 USA

Van Lanen, Steven G.
论文数: 0 引用数: 0
h-index: 0
机构: Boston Coll, Dept Chem, Eugene F Merkert Chem Ctr, Chestnut Hill, MA 02467 USA

Shen, Ben
论文数: 0 引用数: 0
h-index: 0
机构: Boston Coll, Dept Chem, Eugene F Merkert Chem Ctr, Chestnut Hill, MA 02467 USA

Bruner, Steven D.
论文数: 0 引用数: 0
h-index: 0
机构:
Boston Coll, Dept Chem, Eugene F Merkert Chem Ctr, Chestnut Hill, MA 02467 USA Boston Coll, Dept Chem, Eugene F Merkert Chem Ctr, Chestnut Hill, MA 02467 USA
[5]
Mechanistic, Mutational, and Structural Evaluation of a Taxus Phenylalanine Aminomutase
[J].
Feng, Lei
;
Wanninayake, Udayanga
;
Strom, Susan
;
Geiger, James
;
Walker, Kevin D.
.
BIOCHEMISTRY,
2011, 50 (14)
:2919-2930

Feng, Lei
论文数: 0 引用数: 0
h-index: 0
机构:
Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA

Wanninayake, Udayanga
论文数: 0 引用数: 0
h-index: 0
机构:
Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA

Strom, Susan
论文数: 0 引用数: 0
h-index: 0
机构:
Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA

Geiger, James
论文数: 0 引用数: 0
h-index: 0
机构:
Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA

Walker, Kevin D.
论文数: 0 引用数: 0
h-index: 0
机构:
Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA
Michigan State Univ, Dept Biochem & Mol Biol, E Lansing, MI 48824 USA Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA
[6]
β-styryl- and β-aryl-β-alanine products of phenylalanine aminomutase catalysis
[J].
Klettke, Karin L.
;
Sanyal, Sanjit
;
Mutatu, Washington
;
Walker, Kevin D.
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2007, 129 (22)
:6988-+

Klettke, Karin L.
论文数: 0 引用数: 0
h-index: 0
机构: Michigan State Univ, Dept Chem & Biochem, E Lansing, MI 48824 USA

Sanyal, Sanjit
论文数: 0 引用数: 0
h-index: 0
机构: Michigan State Univ, Dept Chem & Biochem, E Lansing, MI 48824 USA

Mutatu, Washington
论文数: 0 引用数: 0
h-index: 0
机构: Michigan State Univ, Dept Chem & Biochem, E Lansing, MI 48824 USA

Walker, Kevin D.
论文数: 0 引用数: 0
h-index: 0
机构: Michigan State Univ, Dept Chem & Biochem, E Lansing, MI 48824 USA
[7]
Discovery of Additional Members of the Tyrosine Aminomutase Enzyme Family and the Mutational Analysis of CmdF
[J].
Krug, Daniel
;
Mueller, Rolf
.
CHEMBIOCHEM,
2009, 10 (04)
:741-750

Krug, Daniel
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Saarland, Dept Pharmaceut Biotechnol, D-66041 Saarbrucken, Germany Univ Saarland, Dept Pharmaceut Biotechnol, D-66041 Saarbrucken, Germany

Mueller, Rolf
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Saarland, Dept Pharmaceut Biotechnol, D-66041 Saarbrucken, Germany Univ Saarland, Dept Pharmaceut Biotechnol, D-66041 Saarbrucken, Germany
[8]
Gatekeeping versus promiscuity in the early stages of the andrimid biosynthetic assembly line
[J].
Magarvey, Nathan A.
;
Fortin, Pascal D.
;
Thomas, Paul M.
;
Kelleher, Neil L.
;
Walsh, Christopher T.
.
ACS CHEMICAL BIOLOGY,
2008, 3 (09)
:542-554

Magarvey, Nathan A.
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Dept Biol Chem & Mol Pharmacol, Sch Med, Boston, MA 02115 USA Harvard Univ, Dept Biol Chem & Mol Pharmacol, Sch Med, Boston, MA 02115 USA

Fortin, Pascal D.
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Dept Biol Chem & Mol Pharmacol, Sch Med, Boston, MA 02115 USA Harvard Univ, Dept Biol Chem & Mol Pharmacol, Sch Med, Boston, MA 02115 USA

Thomas, Paul M.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Illinois, Dept Chem, Urbana, IL 61801 USA Harvard Univ, Dept Biol Chem & Mol Pharmacol, Sch Med, Boston, MA 02115 USA

Kelleher, Neil L.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Illinois, Dept Chem, Urbana, IL 61801 USA Harvard Univ, Dept Biol Chem & Mol Pharmacol, Sch Med, Boston, MA 02115 USA

Walsh, Christopher T.
论文数: 0 引用数: 0
h-index: 0
机构:
Harvard Univ, Dept Biol Chem & Mol Pharmacol, Sch Med, Boston, MA 02115 USA Harvard Univ, Dept Biol Chem & Mol Pharmacol, Sch Med, Boston, MA 02115 USA
[9]
Unusual mechanism for an aminomutase rearrangement: Retention of configuration at the migration termini
[J].
Mutatu, Washington
;
Klettke, Karin L.
;
Foster, Clifton
;
Walker, Kevin D.
.
BIOCHEMISTRY,
2007, 46 (34)
:9785-9794

论文数: 引用数:
h-index:
机构:

Klettke, Karin L.
论文数: 0 引用数: 0
h-index: 0
机构: Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA

Foster, Clifton
论文数: 0 引用数: 0
h-index: 0
机构: Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA

Walker, Kevin D.
论文数: 0 引用数: 0
h-index: 0
机构:
Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA
[10]
Biosynthesis of (R)-β-tyrosine and its incorporation into the highly cytotoxic chondramides produced by Chondromyces crocatus
[J].
Rachid, Shwan
;
Krug, Daniel
;
Weissman, Kira J.
;
Mueller, Rolf
.
JOURNAL OF BIOLOGICAL CHEMISTRY,
2007, 282 (30)
:21810-21817

Rachid, Shwan
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Saarland, Inst Pharmaceut Biotechnol, D-66041 Saarbrucken, Germany Univ Saarland, Inst Pharmaceut Biotechnol, D-66041 Saarbrucken, Germany

Krug, Daniel
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Saarland, Inst Pharmaceut Biotechnol, D-66041 Saarbrucken, Germany Univ Saarland, Inst Pharmaceut Biotechnol, D-66041 Saarbrucken, Germany

Weissman, Kira J.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Saarland, Inst Pharmaceut Biotechnol, D-66041 Saarbrucken, Germany Univ Saarland, Inst Pharmaceut Biotechnol, D-66041 Saarbrucken, Germany

Mueller, Rolf
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Saarland, Inst Pharmaceut Biotechnol, D-66041 Saarbrucken, Germany Univ Saarland, Inst Pharmaceut Biotechnol, D-66041 Saarbrucken, Germany