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Stereochemistry of the reactions catalyzed by chicken liver fatty acid synthase.

Publication ,  Journal Article
Anderson, VE; Hammes, GG
Published in: Biochemistry
April 24, 1984

The stereochemistry of the four partial reactions catalyzed by chicken liver fatty acid synthase that lead to the synthesis of palmitic acid has been determined. The reduction of acetoacetyl-CoA to 3-hydroxybutyryl-CoA by NADPH proceeds with the transfer of the pro-4S hydrogen of NADPH to form D-3-hydroxybutyryl-CoA. During the subsequent dehydration of D-3-hydroxybutyryl-CoA the pro-2S hydrogen and the 3-hydroxyl group are removed in a syn elimination to form crotonyl-CoA. Crotonyl-CoA is reduced to butyryl-CoA by NADPH, with the transfer of the pro-4R hydrogen of NADPH to the pro-3R position in butyryl-CoA and the transfer of a solvent hydrogen to the pro-2S position. The occurrence of the syn dehydration, when combined with the results of a previous study [ Sedgwick , B., & Cornforth , J. W. (1977) Eur. J. Biochem. 75, 465-479], implies that the condensation of the enzyme-bound malonyl moiety with the enzyme-bound saturated fatty acid to form a 3-keto intermediate proceeds with inversion at C-2 of the malonyl. The stereochemistry of the hydration was derived from an analysis of the spin-spin coupling constant of 3-hydroxy[2-2H]butyric acid benzylamides obtained from 3-hydroxy[2-2H]butyryl-CoA synthesized by fatty acid synthase. The elucidation of the stereochemistry of the reduction of crotonyl-CoA relied on the previously established stereochemistry of pork liver acyl-CoA dehydrogenase. The source of all 28 prochiral hydrogens of the palmitic acid synthesized by chicken liver fatty acid synthase was inferred from the results of this work.

Duke Scholars

Published In

Biochemistry

DOI

ISSN

0006-2960

Publication Date

April 24, 1984

Volume

23

Issue

9

Start / End Page

2088 / 2094

Location

United States

Related Subject Headings

  • Stereoisomerism
  • Palmitic Acids
  • Palmitic Acid
  • Oxidation-Reduction
  • NADP
  • Liver
  • In Vitro Techniques
  • Fatty Acid Synthases
  • Chickens
  • Biochemistry & Molecular Biology
 

Citation

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MLA
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Anderson, V. E., & Hammes, G. G. (1984). Stereochemistry of the reactions catalyzed by chicken liver fatty acid synthase. Biochemistry, 23(9), 2088–2094. https://doi.org/10.1021/bi00304a033
Anderson, V. E., and G. G. Hammes. “Stereochemistry of the reactions catalyzed by chicken liver fatty acid synthase.Biochemistry 23, no. 9 (April 24, 1984): 2088–94. https://doi.org/10.1021/bi00304a033.
Anderson VE, Hammes GG. Stereochemistry of the reactions catalyzed by chicken liver fatty acid synthase. Biochemistry. 1984 Apr 24;23(9):2088–94.
Anderson, V. E., and G. G. Hammes. “Stereochemistry of the reactions catalyzed by chicken liver fatty acid synthase.Biochemistry, vol. 23, no. 9, Apr. 1984, pp. 2088–94. Pubmed, doi:10.1021/bi00304a033.
Anderson VE, Hammes GG. Stereochemistry of the reactions catalyzed by chicken liver fatty acid synthase. Biochemistry. 1984 Apr 24;23(9):2088–2094.
Journal cover image

Published In

Biochemistry

DOI

ISSN

0006-2960

Publication Date

April 24, 1984

Volume

23

Issue

9

Start / End Page

2088 / 2094

Location

United States

Related Subject Headings

  • Stereoisomerism
  • Palmitic Acids
  • Palmitic Acid
  • Oxidation-Reduction
  • NADP
  • Liver
  • In Vitro Techniques
  • Fatty Acid Synthases
  • Chickens
  • Biochemistry & Molecular Biology