Photo-Activatable Amino Acids
OwnerChristoph Thiele, Monika Suchanekinventors
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Abstract
This invention relates to an amino acid based on a naturally occurring non-polar, non-aromatic α-amino acid, wherein said amino acid differs from the naturally occurring counterpart in that the side chain contains a diazirine ring. Furthermore provided are methods of synthesizing a (poly)peptide with one or more amino acids of the invention incorporated, methods for cross-linking interacting molecules, methods of synthesizing the amino acids of the invention, and a kit comprising the amino acids of the invention.
Claims38
An amino acid based on a naturally occurring non-polar, non-aromatic α-amino acid, wherein said amino acid differs from the naturally occurring counterpart in that the side chain contains a diazirine ring.
A method of synthesizing an amino acid of formula (I), comprising the step of reacting 4,4′-azi-pentanal with NH3, NH4Cl and NaCN.
A method of synthesizing an amino acid of formula (I), comprising the steps of:
- (a) reacting 5-oxo-hexanoic acid with NH3, NH2OSO3H and I2;
- (b) brominating the 5,5′-azi-hexanoic acid obtained in step (a);
- and
- (c) aminolysis of the 2-bromo-5,5′-azi-hexanoic acid obtained in step (b).
A method of synthesizing an amino acid of formula (II), comprising the steps of:
- (a) reacting 4-oxo-pentanoic acid with NH3, NH2OSO3H and (2;
- (b) brominating the 4,4′-azi-pentanoic acid obtained in step (a);
- and
- (d) aminolysis of the 2-bromo-4,4′-azi-pentanoic acid obtained in step (b).
A method of synthesizing an amino acid of formula (III), comprising the steps of:
- (a) reacting 3-methyl-4-oxo-pentanoic acid with NH3, NH2OSO3H and (2;
- (b) brominating the 3-methyl-4,4′-azi-pentanoic acid obtained in step (a);
- and
- (c) aminolysis of the 2-bromo-3-methyl-4,4′-azi-pentanoic acid obtained in step (b).
Dependencies are inferred from the claim text.