A COLLECTION OF 19F-NMR LABELS FOR PEPTIDE STUDIES

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A COLLECTION OF 19F-NMR LABELS FOR PEPTIDE STUDIES
Igor V. Komarov,a Pavel K. Mykhailiuk,a Dmytro S.
Radchenko,b Anton N. Tkachenko,b Oleksiy S.
Artamonov,a Andrii V. Bezdudnyb
a Kiev National Taras Shevchenko University,
Kiev, Ukraine b Enamine Ltd, Kiev, Ukraine,
www.enamine.net
Solid-state NMR of peptides labeled with
19F-substituted amino acids has been established
as an efficient tool of structural studies of the
peptides in biomembranes. Successful application
of this tool critically depends on careful
design, synthesis and incorporation in the
peptides under study the fluorine-substituted
amino acids (F-labels). The design principles
important for the F-labels included molecular
rigidity, maximal similarity to the natural
counterpart, and synthetic availability. Guided
by these principles, we aimed at creation of a
collection of the labels mimicking all the
natural amino acid types.
NEW F-LABELS MIMIC THE NATURAL AMINO ACIDS OF ALL
TYPES
THE KNOWN F-LABELS MIMIC AMINO ACIDS WITH
HYDROPHOBIC SIDE CHAINS
SYNTHESIS HYDROPHOBIC AMINO ACIDS AND A PROLINE
ANALOGUE
SYNTHESIS HYDROPHOBIC AMINO ACID
GLUTAMIC ACID AND ARGININE ANALOGUES
SERINE ANALOGUE