Preface A l p h a - A m i n o acids ( a - A A s ) are indispensable building blocks o f life, as we know it on this planet, and one o f a few classes o f organic Downloaded by 80.82.77.83 on December 24, 2017 | http://pubs.acs.org Publication Date: June 14, 2009 | doi: 10.1021/bk-2009-1009.pr001
compounds with recognition in the street. Besides their primary function as structural units o f peptides and proteins, they also serve countless biological
functions
in most
living
things. Thus, apart
from
20
proteinogenic/coded a - A A s , hundreds o f structurally varied a - A A s have been found in the peptides o f cell walls and capsules o f numerous bacteria and fungi as well as in various natural antibiotics. Furthermore, naturally occurring a - A A s have been continually used as a "chiral p o o l " for the preparation o f a plethora o f biologically and pharmacologically active compounds
and
are
widely
applied in the
pharmaceutical,
agrochemical, and food industries. Tailor-made a - A A s are increasingly employed in the preparation o f new synthetic enzymes, hormones, and immunostimulants. More recently, sterically constrained a - A A s have found fundamental applications in the rational de novo design o f peptides and peptidomimetics with enhanced metabolic stability and physiological functions. The structural diversity, biological activity, and application o f a - A A s in organic synthesis, biochemistry, food, fragrances, and healthrelated sciences are far too broad to be covered in a single review. O n the other hand, this brief introductory text might convince the reader that aA A s have been and continue to be at the forefront o f organic-synthesis science because o f their remarkable impact on virtually every bio-related industrial and academic endeavor. Chemistry and various applications o f a - A A s have been the subject o f numerous review articles over the years, following the first and only comprehensive treatment o f this subject published by Professor Robert M . Williams in 1989. However, each review article typically focuses on a particular aspect o f synthesis or application o f a - A A s , leaving aside other
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Soloshonok and Izawa; Asymmetric Synthesis and Application of -Amino Acids ACS Symposium Series; American Chemical Society: Washington, DC, 2009.
aspects o f a - A A s science. This book represents, for the first time, an attempt to give the reader a snapshot o f the most active and promising current research activity in the general
field
o f a - A A s , instead o f
collecting comprehensive data on a particular aspect. We hope this book w i l l convey to the reader the vibrant breadth and ingenuity o f the current research in the area o f asymmetric synthesis, and w i l l prove to be both deeply instructive and stimulating. This
book
is derived
from the
A C S Symposium
Synthesis of a-Amino Acids. Novel Developments
Asymmetric
and Future
Directions,
rd
as part o f the 2 3 3 American Chemical Society ( A C S ) National Meeting, Downloaded by 80.82.77.83 on December 24, 2017 | http://pubs.acs.org Publication Date: June 14, 2009 | doi: 10.1021/bk-2009-1009.pr001
M a r c h 25-29, 2007, Chicago, Illinois, featuring 11 speakers from 6 countries. In the design o f this book, we decided to invite contributions from 17 more leading scientists in the field, to give the reader a more complete overview o f current ideas and potential in a - A A research. Moreover, we decided to emphasize the current state o f the art in the industrial
production
contributions from
of
several
enantiomerically
pure
a-AA,
leading industry researchers.
inviting
The
book
consists o f four general sub-topics, including Stoichiometric, Catalytic and Enzymatic approaches for the preparation o f enantiomerically pure a - A A , application o f a - A A s in the total synthesis o f complex natural products, and one chapter on the most advanced and innovative, in our opinion, approach for preparation o f a-peptides. O f particular interest to us as editors is that many o f the data the reader w i l l find in this book have not been previously published, rendering this volume a prime source for new and stimulating research data. As
organizers o f the symposium and editors o f this book, we
gratefully acknowledge the truly outstanding contributions from
11
speakers at the symposium and 28 authors o f the book, all o f whom have made our work both enjoyable and highly rewarding. Finally,
it is w i t h
great pleasure
that we a c k n o w l e d g e
the
leadership o f the A C S D i v i s i o n o f O r g a n i c C h e m i s t r y for g i v i n g us an
opportunity
generous
to organize
financial
support.
the
S y m p o s i u m and
We are
also
grateful
for p r o v i d i n g to the A C S
D i v i s i o n o f M e d i c i n a l C h e m i s t r y for c o s p o n s o r i n g the S y m p o s i u m and for their generous f i n a n c i a l support. O u r particular thanks go to the A j i n o m o t o C o m p a n y , Inc. ( T o k y o , Japan) for their prominent
xii
Soloshonok and Izawa; Asymmetric Synthesis and Application of -Amino Acids ACS Symposium Series; American Chemical Society: Washington, DC, 2009.
and
e n c o u r a g i n g support and for p r o v i d i n g the major
financ
contribution to the S y m p o s i u m .
Vadim A. Soloshonok Department o f Chemistry The University o f Oklahoma 620 Parrington O v a l , Room 208 Norman, OK 73019-3051
Downloaded by 80.82.77.83 on December 24, 2017 | http://pubs.acs.org Publication Date: June 14, 2009 | doi: 10.1021/bk-2009-1009.pr001
Kunisuke Izawa AminoScience Laboratories A m i n o A c i d s Company Ajinomoto C o . , Inc. 1-1 Suzuki-cho, Kawasaki-ku Kawasaki-shi 210-8681, Japan
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Soloshonok and Izawa; Asymmetric Synthesis and Application of -Amino Acids ACS Symposium Series; American Chemical Society: Washington, DC, 2009.
