I would add this qualifier to Roger's suggestion. If you have multiple
lysines in your synthesis target I would use Fmoc-Lys(ivDde)-OH available
from NovaBiochem. Migration of Dde protecting group from one Lysine to
another (during Fmoc removal with piperidine) has been shown:
Augustyns, K., Kraas, W., and Jung, G., J. Peptide Res., 51, 127 (1998).
Chhabra, et al. have examined the Fmoc-Lys(Dde)-OH vs. the ivDde protected
form and found that the ivDde effectively inhibits the migration from one
lysine to another.
Chhabra, S. R., Hothi, B., Evans, D. J., White, P. D., Bycroft, B. W. and
Chan, W. C., Tet. Lett., 39, 1603 (1998).
We have repeated this in our labs with the same finding. We have also
studied Fmoc-Lys-Dpr(Dde)-OH vs. Fmoc-Lys(ivDde)-OH, and examined
Fmoc-Dab(ivDde)-OH for such migrations. This work is not yet published, but
I can say that the Fmoc-Dpr(Dde)-OH showed migrations of the protecting
group from the beta to the alpha amine of Dpr during fmoc removal. Isomeric
peptides result from this route of synthesis with extension off both the
alpha and beta amine of Dpr.
Srinivasan, A., Wilhelm, R. R., Schmidt, M. A., Peptides: Frontiers of
Peptide Science, Proc. of 15th APS, 269 (1999).
Randy Wilhelm
Sr. Research Chemist
Mallinckrodt, Inc
Discovery Research Peptide Team
Phone (314)654-3965
Fax (314)654-8911
rrwilhe@mkg.com
> ----------
> From: Roger Murphy[SMTP:Roger.Murphy@ludwig.edu.au]
> Sent: Thursday, November 04, 1999 4:11 PM
> To: Recipients of ABRF List
> Cc: abrf@aecom.yu.edu
> Subject: Re: Lysine
>
> Bob,
>
> Much the same answer as per your selective deprotection of Glu - use
> Fmoc-Lys(Dde)-OH and deprotect with 2% hydrazine in DMF. I've used it and
>
> it works well.
>
> Roger
>
> At 08:58 04/11/99 -0500, you wrote:
> >abrf@aecom.yu.edu
>
>
> ------------------------------------------------------------
> Roger Murphy, Ph.D.
> Biological Production Facility
> Ludwig Institute for Cancer Research
> Austin & Repatriation Medical Centre
> Studley Road,
> Heidelberg, Vic. 3084
> Australia.
>
> Tel 61-3-94965463
> Fax 61-3-94965436
> Email Roger.Murphy@Ludwig.edu.au
>