Photolabile linker for the solid-phase synthesis of hydrazides and pyranopyrazoles
AssigneeDanmarks Tekniske Universitet
InventorsThomas E. Nielsen, Katrine Qvortrup
Life of this patent
Estimating the term…
Abstract
The photolabile hydrazine linker of the present invention is based on the o-nitro-veratryl group, which is capable of releasing hydrazide derivatives upon UV irradiation. The linker allows for a new solid-phase peptide synthesis (SPPS) strategy which is fully orthogonal to the most commonly used protecting groups and chemical methods in SPPS and shows excellent compatibility with peptide composition, notably the 20 naturally occurring α-amino acid residues (even in their side-chain protected form) are accepted in the C-terminal of the peptide hydrazides. Furthermore, the linker unit can be applied to synthesize combinatorial libraries of biological interesting heterocyclic compounds, such as pyranopyrazoles.
Claims18
A photolabile hydrazine linker having the formula I:
- wherein R* is OR′, wherein R′ is hydrogen, C1-12 alkyl, substituted C1-10 alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl or —(CH2—CH2—O)—m;
- R is hydrogen or a protection group;
- m is an integer from 1-100;
- and n is an integer from 1 to 10.
A solid phase having a formula of:
- wherein
- is a functionalized solid support;
- is a photolabile hydrazine linker, wherein n is an integer from 1 to 10;
- and
- PG is a protecting group.
A solid phase having a formula of:
- wherein
- is a functionalized solid support,
- is a photolabile hydrazine linker, wherein n is an integer from 1 to 10;
- and
- the connection between the solid support and the photolabile hydrazine linker optionally comprises a spacer and/or an orthogonally cleavable linker.
Dependencies are inferred from the claim text.