Novel Cofactors

A cofactor is a component part of many enzymes and functions by uniting with another molecule in order to become active. The use of cofactors to supplement the native amino acids of a protein is essential to maintain the chemical capabilities necessary for organisms to survive. This volume focuses on the significant advances of the past decade in identifying and describing new cofactors--either small molecules or those derived posttranslationally.

Preface

ix

Radical Mechanisms of S-Adenosylmethionine-Dependent Enzymes

Perry A. Frey

Squire J. Booker

Introduction

1

(1)

Lysine 2,3-Aminomutase

2

(17)

Pyruvate Formate-Lyase

19

(7)

Anaerobic Ribonucleotide Reductase

26

(6)

Biotin Synthase

32

(6)

Lipoic Acid Biosynthesis

38

(9)

References

42

(5)

Molybdopterin from Molybdenum and Tungsten Enzymes

Hermann Schindelin

Caroline Kisker

K. V. Rajagopalan

Introduction

47

(3)

Mo/W Cofactor Containing Enzymes

50

(27)

Cofactor Biosynthesis

77

(18)

References

90

(5)

Pyrroloquinoline Quinone (PQQ) from Methanol Dehydrogenase and Tryptophan Tryptophylquinone (TTQ) from Methylamine Dehydrogenase

Victor L. Davidson

Introduction

95

(1)

Pyrroloquinoline Quinone (PQQ)

96

(2)

Methanol Dehydrogenase (MEDH)

98

(14)

Tryptophan Tryptophylquinone (TTQ)

112

(1)

Methylamine Dehydrogenase (MADH)

112

(23)

Summary and Perspectives

135

(6)

References

136

(5)

Trihydroxyphenylalanine Quinone (TPQ) from Amine Oxidases and Lysyl Tyrosylquinone (LTQ) from Lysyl Oxidase

Joanne E. Dove

Judith P. Klinman

Introduction

141

(2)

Topa Quinone (TPQ)

143

(1)

Copper Amine Oxidases

143

(21)

Lysine Tyrosylquinone (LTQ)

164

(1)

Lysyl Oxidase

165

(5)

Perspective and Future Directions

170

(5)

References

172

(3)

Methylidence-Imidazolone (MIO) from Histidine and Phenylalanine Ammonia-Lyase

Birgid Langer

Martin Langer

Janos Retey

Introduction

175

(1)

The Metabolic Role of Histidine Ammonia-Lyase and Its Genetic Organization

176

(3)

The Role of Phenylalanine Ammonia-Lyase in Plant Metabolism

179

(1)

Elimination of Ammonia from α-Amino Acids as a Chemical Challenge

180

(2)

History of the Prosthetic Group of HAL and PAL

182

(2)

Origin of the Electrophilic Group

184

(2)

Discovery of MIO by Elucidation of the Crystal Structure of HAL

186

(4)

The Role of the Electrophilic Group in the Catalysis of HAL and PAL

190

(5)

Cloning, Sequencing, and Overexpression of HAL and PAL

195

(1)

The Role of Active-Site Amino Acids as Evaluated by Site-Directed Mutagenesis

196

(6)

Inhibitors of HAL and PAL: Structure and Mechanism of Formation of the Chromophore in the Inhibited HAL

202

(7)

The Use of PAL as Biocatalyst

209

(6)

References

211

(4)

Structural, Redox, and Mechanistic Parameters for Cysteine-Sulfenic Acid Function in Catalysis and Regulation

Al Claiborne

T. Conn Mallett

Joanne I. Yeh

James Luba

Derek Parsonage

Introduction

215

(2)

The Chemistry and Reactions of Sulfenic Acids

217

(6)

Sulfenic Acids in Proteins: The Basics

223

(4)

FAD-Dependent Peroxide and Disulfide Reductases

227

(21)

NO-Inhibition Mechanisms and Reductive Activation of Pt (IV) Anticancer Drugs

248

(8)

Peroxiredoxins and H2O2 as an Intracellular Signaling Molecule

256

(10)

Redox Regulation of Transcription Factors

266

(4)

Summary and Conclusions

270

(7)

References

272

(5)

Stable Glycyl Radical from Pyruvate Formate-Lyase and Ribonucleotide Reductase (III)

Joachim Knappe

A. F. Volker Wagner

Introduction

277

(4)

Properties of Protein-Based Glycyl Radicals

281

(11)

Proposed Catalytic Mechanisms

292

(6)

Posttranslational Production of the Glycyl Radical

298

(8)

Phylogenetic Distribution and Functional Diversity of Glycyl Radical Enzymes

306

(3)

Conclusion and Outlook

309

(8)

References

309

(8)

Tyrosyl Radical Cofactors

Russell P. Pesavento

Wilfred A. Van Der Donk

Introduction

317

(1)

General Properties of Tyrosyl Radicals

318

(1)

Structure, Stability, and Spectroscopy of Tyrosyl Radical Cofactors

318

(24)

Functional Roles of Tyrosyl Radicals in Enzymatic Catalysis

342

(21)

Mechanisms of Generation of the Tyrosyl Radical Cofactor

363

(12)

Summary and Outlook

375

(12)

References

375

(12)

Posttranslationally Modified Tyrosines from Galactose Oxidase and Cytochrome c Oxidase

Melanie S. Rogers

David M. Dooley

Introduction

387

(3)

Galactose Oxidase

390

(27)

Cytochrome c Oxidase

417

(14)

Final Comments

431

(6)

References

432

(5)

Author Index

437

(28)

Subject Index

465

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Summary

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Novel Cofactors

Summary

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