Asymmetric Synthesis and Application of α-Amino Acids - American

found fundamental applications in the rational de novo design of peptides and peptidomimetics with enhanced ... review article typically focuses on a ...
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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.