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US 2026/0226103 A1Published application
Modified amino acids and uses thereof
AssigneeUniversity of Strathclyde
InventorsGlenn BURLEY, Jack ROBERTSON, Fergus Stewart MCWHINNIE
Life of this patent
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Abstract
The present disclosure relates to modified amino acids which have been modified to modulate their physicochemical properties. The present disclosure further relates to the use of such modified amino acids to provide peptides, in particular, cell penetrating peptides with modified physicochemical properties.
Claims29
A cell penetrating peptide comprising at least one modified amino acid residue according to formula (II):
- wherein R1 is selected from H, protecting group and an amino acid residue;
- R8 is selected from H and an amino acid residue;
- X is absent, or is selected from optionally substituted C1-C6 alkyl, optionally substituted —C1-C6 alkyl-NR2(C═O)—, and optionally substituted —C1-C6 alkyl-(C═O)NR2—;
- R2 is selected from H, optionally substituted C1-C6 alkyl and protecting group;
- and
- wherein A is selected from:
- wherein B is selected from optionally substituted aryl, optionally substituted heteroaryl and optionally substituted C1-C6 alkyl;
- Y is absent or NH;
- wherein R3 is selected from H, optionally substituted C1-C6 alkyl and protecting group;
- with the proviso that Y is absent when B is optionally substituted C1-C6 alkyl;
- or
- (ii) a bicyclic fused ring system comprising an amidine-like motif according to the following formula:
- wherein R4 and R6 are each independently selected from H and a carbon atom that forms part of a backbone of the bicyclic ring system;
- R5 is selected from H and protecting group;
- and
- R7 is a carbon atom that forms part of a backbone of the bicyclic ring system;
- wherein the at least one modified amino acid residue is not derived from a modified amino comprising the following structure:
14 more elements
(canceled)
(canceled)
(canceled)
-26. (canceled)
A modified amino acid according to formula (I″):
- wherein:
- R1 is H or protecting group;
- R8 is H or protecting group;
- and
- (i) X is selected from optionally substituted C2-C4 alkyl, optionally substituted —C1-C3 alkyl-NR2(C═O)— and optionally substituted C1-C3 alkyl-(C═O)NR2—;
- R2 is selected from H, optionally substituted C1-C6 alkyl and protecting group;
- and A is:
- wherein B is selected from optionally substituted aryl, optionally substituted heteroaryl and optionally substituted C1-C6 alkyl (such as C1-C3 alkyl);
- Y is absent;
- R3 is selected from H, optionally substituted C1-C6 alkyl and protecting group;
- or
- (ii) X is absent, or is selected from optionally substituted C1-C6 alkyl (e.g. C1-C3 alkyl), optionally substituted —C1-C6 alkyl-NR2(C═O)— (e.g. —C1-C3 alkyl-NR2(C═O)—), and optionally substituted C1-C6 alkyl-(C═O)NR2— (e.g. C1-C3 alkyl-(C═O)NR2—);
- R2 is selected from H, optionally substituted C1-C6 alkyl and protecting group;
- and
- A is selected from:
- wherein R5a is selected from H and protecting group.
13 more elements
-30. (canceled)
-33. (canceled)
Dependencies are inferred from the claim text.