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US 12,723,059 B2Granted
Multicyclic peptides and methods for their preparation
AssigneeUniversiteit Van Amsterdam
InventorsGaston Julia Johannes Richelle, Dieuwertje Emma Streefkerk, Jan Herman Van Maarseveen, Peter Timmerman
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Abstract
The invention relates to methods for preparing a compound comprising a peptide attached to a molecular scaffold whereby multiple peptide loops are formed, to compounds that can be obtained with such methods and uses thereof.
Claims4
A molecular scaffold comprising:
- an aromatic cyclic or heteroaromatic cyclic moiety,
- two or three halides capable of participating in a thiolate nucleophilic substitution reaction, wherein each of said two or three halides capable of participating in a thiolate nucleophilic substitution reaction is attached to an activated methylene group directly attached to the same said aromatic cyclic or heteroaromatic cyclic moiety, and
- two or three reactive groups capable of participating in a reaction selected from the group consisting of an oxime-ligation reaction, an alkyne-azide cycloaddition, a hydrazone ligation reaction and a ring-closing metathesis reaction, wherein each of said two or three reactive groups capable of participating in a reaction selected from the group consisting of an oxime-ligation reaction, an alkyne-azide cycloaddition, a hydrazone ligation reaction and a ring-closing metathesis reaction is directly or indirectly attached to said aromatic cyclic or heteroaromatic cyclic moiety,
- whereby said molecular scaffold possesses C2v symmetry or D3h symmetry with the proviso that the scaffold is not 1,3,5-tris(bromomethyl)-2,4,6-tris(trimethylsilylethynyl)benzene.
1 more element
A molecular scaffold comprising:
- an aromatic cyclic or heteroaromatic cyclic moiety, a 6-membered cycloalkyl, or a 6-membered cycloalkylene,
- two halides capable of participating in a thiolate nucleophilic substitution reaction, wherein, each of said two halides capable of participating in a thiolate nucleophilic substitution reaction is attached to an activated methylene group directly attached to the same said aromatic cyclic or heteroaromatic cyclic moiety,
- two reactive groups capable of participating in a reaction selected from the group consisting of an oxime-ligation reaction, an alkyne-azide cycloaddition, a hydrazone ligation reaction and a ring-closing metathesis reaction, wherein each of said two reactive groups capable of participating in a reaction selected from the group consisting of an oxime-ligation reaction, an alkyne-azide cycloaddition, a hydrazone ligation reaction and a ring-closing metathesis reaction is directly or indirectly attached to said aromatic cyclic or heteroaromatic cyclic moiety, to said 6-membered cycloalkyl, or to said 6-membered cycloalkylene, and
- a freely rotatable bond located between a part of the scaffold that contains said two halides and a part of the scaffold that contains said two reactive groups,
- whereby said molecular scaffold possesses C2v symmetry with the proviso that the scaffold is not 1,3,5-tris(bromomethyl)-2,4,6-tris(trimethylsilylethynyl)benzene.
2 more elements
Dependencies are inferred from the claim text.