Chiral Amplification of Oligopeptides in Two-Dimensional Crystalline Self-Assemblies on Water
Helmut Zepik,1
Edna Shavit,1
Mao Tang,1
Torben R. Jensen,2
Kristian Kjaer,2
Gérard Bolbach,3
Leslie Leiserowitz,1*
Isabelle Weissbuch,1*
Meir Lahav1*
Differences in the two-dimensional packing arrangements of racemic
and enantiomeric crystalline self-assemblies on the water surface of
amphiphilic activated analogs of lysine and glutamic acid have been
used to prepare oligopeptides of homochiral sequence and oligopeptides
of single handedness from chiral nonracemic mixtures. The crystalline
structures on the water surface were determined by grazing incidence
x-ray diffraction and the diastereomeric composition of the
oligopeptides by matrix-assisted laser desorption time-of-flight mass
spectrometry with enantio-labeling. These results suggest that
reactivity of ordered clusters at interfaces might have played a role
in the generation of early homochiral biopolymers.
1 Department of Materials and Interfaces,
Weizmann Institute of Science, 76100 Rehovot, Israel.
2 Materials Research Department, Risø National
Laboratory, 4000 Roskilde, Denmark.
3 Laboratoire de
Chimie Structurale Organique et Biologique, Université Pierre et
Marie Curie, 75252 Paris Cedex 05, France.
*
To whom correspondence should be addressed. E-mail:
leslie.leiserowitz{at}weizmann.ac.il,
isabelle.weissbuch{at}weizmann.ac.il, meir.lahav{at}weizmann.ac.il
