Book of Abstracts - Ruhr-Universität Bochum

P-14
ISBOMC `10 5.7 – 9.7. 2010 Ruhr-Universität Bochum
Coordination of a Peptide �-Turn Mimetic to Tungsten:
Possible Applications for the Study of �-Sheets
Adam N. Boynton a and Timothy P. Curran *a
a Department of Chemistry, Trinity College, Hartford, CT 06106 USA
Email: timothy.curran@trincoll.edu
In 1995 Kemp and Li described the synthesis of 2-amino-2'-carboxyphenylacetylene (1) and its use as
a peptide turn mimetic. 1,2 Their work showed that 1 does function as a �-turn mimetic, and that
1
peptide derivatives incorporating 1 adopted �-sheet structures. A key structural element in 1 is the
alkyne group that links both phenyl rings. Because of our ongoing interest in the use of tungstenalkyne
coordination for generating constrained peptides, 3,4,5 we have begun investigations into whether
peptide derivatives of 1 can be reacted with W(CO)3(dmtc)2 to yield tungsten-bis(alkyne) complexes
(like 2), and whether the peptides maintain a �-sheet structure after coordination to tungsten. If the
peptides do maintain their sheet structure, then it would be of interest to know whether the two �sheets
interact with each other via stacking arrangements. Owing to solubility and oligomerization
issues, there are very few model systems for investigating �-sheet stacking interactions.
2
N
H
O
O
N
H
H
N
O
O
H
N
S
S S
W
S
O
H
N
H
N
O
72
O
N
H
O
NH 2
N
H
O
OH
S S
=
H3C S
N
H3C S
This presentation will detail the status of our efforts to prepare and study these novel
bioorganometallic species.
References
1. D. S. Kemp, Z. Q. Li, Tetrahedron Lett., 1995, 36, 4175-4178.
2. D. S. Kemp, Z. Q. Li, Tetrahedron Lett., 1995, 36, 4179-4180.
3. T. P. Curran, A. L. Grant, R. L. Lucht, J. C. Carter, J. Affonso, Org. Lett., 2002, 4, 2917-2920.
4. T. P. Curran, R. S. H. Yoon, B. R. Volk, J. Organometallic Chem., 2004, 689, 4837-4847.
5. T. P. Curran, A. B. Lesser, R. S. H. Yoon, J. Organometallic Chem., 2007, 692, 1243-1254.