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US 9,359,400 B2Granted
Site-specific chemoenzymatic protein modifications
AssigneeNovartis AG
InventorsAimee Usera, Zachary Robinson, Jennifer Cobb
Life of this patent
Estimating the term…
Abstract
The present invention relates to methods and reagents for use in site-selective modification of proteins having lysine residues with functionalized peptides using a chemoenzymatic microbial transglutaminase-mediated reaction. The functionalized proteins may be used for study or therapeutic uses.
Claims9
A compound of the formula R1-(Leu)x-Gln-(Gly)y-(A-W-B-R2) z wherein x is 0 or 1;
- y is 0 or 1;
- z is 0 or 1;
- R1 is selected from the group consisting of:
- wherein R4 is selected from —H, —N3, and
- W is selected from:
- C1-C6 linear or branches alkyl or polyethylene glycol having a molecular weight of between about 40 and about 80,000 amu;
- A is absent or selected from —O—, —NH—, and —S—;
- B is absent or selected from —O—, —C(O)—, —NH—, —C(O)NH—, —NHC(O)—, —NHC(O)O—, —OC(O)NH—, —OC(O)O—, —C═N(OH)—, —S(O2)—, —NHS(O2)—, —S(O2)NH—, —S(O)—, —NHS(O)—, —S(O)NH—;
- —C(O)O—, —OC(O)—, —S—, ═NH—O—, ═NH—NH— and ═NH—N(C1-C20alkyl)-;
- R2 is selected from the group consisting of:
- a fatty acid, linear or branched C1-C3 alkyl-N3, cyclooctynyl, polysaccharide, —CH(OCH3)2,
- each n is an integer independently selected from 0 to 6;
- and each Q is selected from H and —NO2.
10 more elements
A compound selected from the group consisting of:
A compound of the formula R1-(Leu)x-Gln-(Gly)y-(A-W-B-R2)z wherein x is 0 or 1;
- y is 0 or 1;
- z is 0 or 1;
- R1 is selected from the group consisting of:
- wherein R4 is selected from —H, —N3, and
- W is a polyethylene glycol having a molecular weight of between about 40 and about 80,000 amu;
- A is absent or selected from —O—, —NH—, and —S—;
- B is absent or selected from —O—, —C(O)—, —NH—, —C(O)NH—, —NHC(O)—, —NHC(O)O—, —OC(O)NH—, —OC(O)O—, —C═N(OH)—, —S(O2)—, —NHS(O2)—, —S(O2)NH—, —S(O)—, —NHS(O)—, —S(O)NH—;
- —C(O)O—, —OC(O)—, —S—, ═NH—O—, ═NH—NH— and ═NH—N(C1-C20alkyl)-;
- R2 is a fluorophore;
- and
- each Q is selected from H and —NO2.
8 more elements
Dependencies are inferred from the claim text.