Asymmetric Synthesis and Application of α-Amino Acids

505 Pages·2009·17.51 MB·English

by  Vadim A. Soloshonok and Kunisuke Izawa (Eds.)

Asymmetric Synthesis and
Application of α-Amino Acids

ACS SYMPOSIUM SERIES 1009
Asymmetric Synthesis and
Application of α-Amino Acids
Vadim A. Soloshonok, Editor
The University of Oklahoma
Kunisuke Izawa, Editor
Ajinomoto Company, Inc.

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Table of Contents
Preface
Vadim A. Soloshonok and Kunisuke Izawa xi-xiii

Stoichiometric Approach

Recent Developments in the Application of Organometallic Chemistry to Amino Acid
Synthesis
Richard F. W. Jackson 2-12

Synthesis of Heterocycle-Linked C-Glycosyl α-Amino Acids and C-Glycopeptides
Alessandro Dondoni and Alessandro Massi 13-30

Asymmetric Synthesis of Amino Acids with a Tetrasubstituted Carbon Center via
Memory of Chirality
Takeo Kawabata 31-56

Asymmetric Synthesis of α-Substituted α-Amino Acids: Strecker and Claisen Approaches
Yasufumi Ohfune, Kazuhiko Sakaguchi, and Tetsuro Shinada 57-71

Michael Addition Reactions between Nucleophilic Glycine Equivalents and Acrylic Acid
Derivatives as a Practical and Generalized Approach to the Asymmetric Synthesis of β-
Substituted-α-Amino Acids
Vadim A. Soloshonok, Hisanori Ueki, and Trevor K. Ellis 72-88

Novel Chiral Template for Preparation of α-Amino Acids: Practical Synthesis and
Application
Kazumi Okuro, Yasuhiro Saka, Ikuhiro Suzuki, and Masaru Mitsuda 89-100

Catalytic Approach

Catalytic Enantioselective Synthesis of α,α-Disubstituted Amino Acids: The Strecker
Reaction of Ketimines Using Chiral Poly-Gadolinium Complexes
Masakatsu Shibasaki and Motomu Kanai 102-115

Asymmetric Amino Acid Synthesis by the Asymmetric Alkylation of Glycine Derivatives
with Chiral Spiro-Type and Simplified Phase-Transfer Catalysts
Keiji Maruoka 116-127

Catalytic Asymmetric Synthesis of α-Amino Acid Derivatives: Approaches toward Green
Sustainable Methodology for Preparation of Optically Active Amino Acids
Yasuhiro Yamashita and Shū Kobayashi 128-155

Transition Metal Catalyzed Reactions toward the Synthesis of Amino Acids and Peptides
Uli Kazmaier 157-176
Development of Phase-Transfer-Catalyzed Asymmetric Strecker Reaction Based on the
Molecular Design of Chiral Quaternary Ammonium Salts
Takashi Ooi 177-189

Efficient Synthesis of α-Amino Acids via Organoboronate Reagents
Nicklas Selander and Kálmán J. Szabó 190-202

Synthesis of Amino Acid Derivatives via Asymmetric Hydrogenation
Hideo Shimizu, Izuru Nagasaki, Noboru Sayo, and Takao Saito 203-226

Stereoselective Synthesis of anti-β-Hydroxy-α-Amino Acids Using anti-Selective
Asymmetric Hydrogenation
Yasumasa Hamada and Kazuishi Makino 227-238

Catalyst Screening for the Synthesis of Amino Acids
David J. Ager, Laurent Lefort, and Johannes G. de Vries 239-250

Asymmetric Synthesis of α-Amino Acids Using Polymer-Supported Cinchona
Ammonium Salts as Phase-Transfer Catalysts
Rafael Chinchílla and Carmen Nájera 251-264

Synthesis and Application of Chiral α-Amino Acids by Kinetic Resolution of Urethane-
Protected α-Amino Acid N-Carboxyanhydrides with Modified Cinchona Alkaloid
Catalysts
Jianfeng Hang, Yutaka Ishii, Yoshiro Furukawa, and Li Deng 265-287

Stereoselective Synthesis of Quaternary, α-Vinyl Amino Acids and Their α-(2'Z-
Fluoro)vinyl Congeners: Promising Candidates for PLP Enzyme Inactivation
David B. Berkowitz, Kannan R. Karukurichi, Roberto de la Salud-Bea, Gourhari Maiti, Jill M.
McFadden, and Michelle L. Morris 288-303

Enzymatic Approach

Preparation of Chiral Amino Acid Intermediates for Synthesis of Pharmaceutical
Compounds Using Amino Acid Dehydrogenases
Ronald L. Hanson 306-321

Chemo-Enzymatic Synthesis of Unnatural Amino Acids
Ian V. Archer, S. Alison Arnold, Reuben Carr, Ian G. Fotheringham, Robert E. Speight, and
Paul P. Taylor 322-336

Integrated Solutions of Unnatural α-Amino Acids
Takahiro Ohishi, Masahiko Yamada, and Masanobu Sugawara 337-356
Enzymatic Synthesis of Unnatural Amino Acids
Mari Hara Yasuda, Makoto Ueda, Kazuya Okano, Hisaaki Mihara, and Nobuyoshi Esaki
357-374
Production of Amino Acids Using Wild Type and Recombinant Whole Cell Catalysts:
Using Platform Technologies for Enhancing Production Efficiency
S. Verseck, U. Becker, K. Doderer, S. Oβwald, and W. Wienand 375-393

Synthesis of Optically Active α-Methyl Amino Acids Using Biotransformation as a Key
Step
Masanobu Yatagai, Takayuki Hamada, Hiroyuki Nozaki, Shinji Kuroda, Kenzo Yokozeki, and
Kunisuke Izawa 394-406

A Novel Method of Amino Acids in a Cell Factory
Motoko Hayashi and Hiroaki Yamamoto 407-417

Application of Enantiomerically Pure α-Amino Acids in the Total Synthesis of Complex
Natural Products and Peptides

New Tricks in Amino Acid Synthesis: Applications to Complex Natural Products
Robert M. Williams and Cameron M. Burnett 420-442

β-Substituted D-Leucines and Their Relevance in the Total Synthesis of Natural and
Unnatural Aeruginosins
Juan R. Del Valle, Xiaotian Wang, Karolina Ersmark, and Stephen Hanessian 443-461

Pure Peptides via Fluorocarbon Capping Technology: A Hands-On Discussion
Vittorio Montanari 462-474

Indexes

Author Index 477

Subject Index 479-490

Color Figure Inserts a-c
Preface
Alpha-Amino acids (a-AAs) are indispensable building blocks of
life, as we know it on this planet, and one of a few classes of organic
compounds with recognition in the street. Besides their primary function
as structural units of peptides and proteins, they also serve countless
biological functions in most living things. Thus, apart from 20
proteinogenic/coded a-AAs, hundreds of structurally varied a-AAs have
been found in the peptides of cell walls and capsules of numerous
bacteria and fungi as well as in various natural antibiotics. Furthermore,
naturally occurring a-AAs have been continually used as a "chiral pool"
for the preparation of a plethora of biologically and pharmacologically
active compounds and are widely applied in the pharmaceutical,
agrochemical, and food industries. Tailor-made a-AAs are increasingly
employed in the preparation of new synthetic enzymes, hormones, and
immunostimulants. More recently, sterically constrained a-AAs have
found fundamental applications in the rational de novo design of peptides
and peptidomimetics with enhanced metabolic stability and physiological
functions. The structural diversity, biological activity, and application of
a-AAs in organic synthesis, biochemistry, food, fragrances, and health-

related sciences are far too broad to be covered in a single review. On the
other hand, this brief introductory text might convince the reader that a-
AAs have been and continue to be at the forefront of organic-synthesis
science because of their remarkable impact on virtually every bio-related

industrial and academic endeavor.
Chemistry and various applications of a-AAs have been the subject
of numerous review articles over the years, following the first and only
comprehensive treatment of this subject published by Professor Robert
M. Williams in 1989. However, each review article typically focuses on a
particular aspect of synthesis or application of a-AAs, leaving aside other
xi