16. Biochemistry of the Cyclopropyl Group

  1. Zvi Rappoport
  1. Hung-Wen Liu1 and
  2. Christopher T. Walsh2

Published Online: 28 JAN 2005

DOI: 10.1002/0470023449.ch16

Cyclopropyl Group: Volume 1 and Volume 2 (1987)

Cyclopropyl Group: Volume 1 and Volume 2 (1987)

How to Cite

Liu, H.-W. and Walsh, C. T. (1987) Biochemistry of the Cyclopropyl Group, in Cyclopropyl Group: Volume 1 and Volume 2 (1987) (ed Z. Rappoport), John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/0470023449.ch16

Editor Information

  1. The Hebrew University, Jerusalem, Israel

Author Information

  1. 1

    Department of Chemistry, University of Minnesota, Minneapolis, MN.55455, USA

  2. 2

    Departments of Chemistry and Biology, Massachusetts Institute of Technology, Cambridge, MA 02139, USA

Publication History

  1. Published Online: 28 JAN 2005
  2. Published Print: 28 OCT 1987

Book Series:

  1. PATAI'S Chemistry of Functional Groups

Book Series Editors:

  1. Saul Patai

ISBN Information

Print ISBN: 9780471917380

Online ISBN: 9780470023440

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Summary

This chapter contains sections titled:

  • Introduction

    • Representative Structures

      • Polyacetates

      • Fatty Acids

      • Amino Acids

      • Polyether Antibiotics

      • Terpenoids

      • Steroids

      • Alkaloids

      • Cyclopropene-containing Compounds

    • Classification by Substitution Patterns

    • Cyclopropyl Groups as Transient Structural Elements in Metabolic Processing

      • Laurinterol to Aplysin

      • Thujopsene to Widdrol

      • Ergosterol Construction of the 5,7-diene Unit

  • Biological Routes to Cyclopropyl Group Construction

    • Cyclopropane Formation by Skeletal Rearrangement of Carbon Framework

      • Biosynthesis of Thujane-type Monoterpenes

      • Biosynthesis of Carane

      • Biosynthesis of Casbene

      • Biosynthesis of Illudins

      • Presqualene Pyrophosphate Biosynthesis

      • Biosynthesis of Phytoene

    • Cyclopropane Formation in Steroids by Participation of the Angular Methyl Group: Squalene to Cycloartenol

    • Cyclopropyl Group Formation via Addition of a One-carbon Fragment from S-Adenosylmethionine

      • Biosynthesis of Steroids with Cyclopropane or Cyclopropene-containing Side Chain

      • Biosynthesis of Cyclopropane-containing Fatty Acids

      • Biogenesis of 1-aminocyclopropane-1-carboxylic Acid (ACPC)

      • Biosynthesis of Hypoglycine A

    • Photo-induced Cyclopropane Formation

  • Biological Degradation of Cyclopropane Rings

    • Degradation of Cyclopropane Rings in the Biosynthesis of Irregular Monoterpenes

    • Ring-opening of Cycloartenol Derivatives

    • Enzymic Fragmentation of 1-Aminocyclopropane-1-carboxylic Acid (ACPC)

      • ACPC Deaminase: ACPC to α-ketobutyrate

      • ACPC Fragmentation to Ethylene

  • Cyclopropyl Substrates and Substrate Analogs Uses as Probes of Enzymatic Mechanisms

    • Naturally Occurring Cyclopropanoid Inactivators of Acyl CoA Dehydrogenase and Aldehyde Dehydrogenase

      • Hypoglycine A

      • Coprine

    • Radical Intermediates as Inactivators in Enzymatic Processing of Cyclopropylcarbinyl and Cyclopropylamino Substrates

      • Monoamine Oxidase Inactivation

      • Liver Microsomal Cytochrome P450 Monooxygenases

      • Quinoprotein Dehydrogenase

    • Cyclopropane Models for NADH Redox Transfer Mechanisms

  • Summary

  • References