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US 12,110,523 B2Granted
Reagents and methods for esterification
AssigneeWisconsin Alumni Research Foundation
InventorsRonald T. Raines, Kalie Mix
Life of this patent
Estimating the term…
Abstract
Methods and reagents for esterification of biological molecules including proteins, polypeptides and peptides. Diazo compounds of formula I: where R is hydrogen, an alkyl, an alkenyl or an alkynyl, RA represents 1-5 substituents on the indicated phenyl ring and RM is an organic group. RM includes a label, a cell penetrating group, a cell targeting group, or a reactive group or latent reactive group for reaction to bond to a label, a cell penetrating group, or a cell targeting group, among other organic groups useful for esterification of biological molecules. Also provided are diazo compounds which are bifunctional and trifunctional coupling reagents as well as reagents for the synthesis of compounds of formula I.
Claims24
A compound of formula I:
- or salts thereof,
- where:
- R is hydrogen, an alkyl group, alkenyl group, or an alkynyl group;
- RM is M or -L-M, where M is a polymer or a non-polymeric organic group, having from 1 to 100 carbon atoms and optionally nitrogen, oxygen or sulfur atoms, and -L is a divalent linker moiety having from 1-30 carbon atoms and optionally nitrogen, oxygen or sulfur atoms;
- and
- RA represents 1 to 3 non-hydrogen substituents on the phenyl ring, wherein the non-hydrogen substituents are selected from the group consisting of alkyl, cycloalkyl, alkoxy, cycloalkoxy, aryl, arylalkyl, haloalkyl, haloalkoxy, heterocyclyl and RP—CO—NH—, where the alkyl, cycloalkyl, alkoxy, cycloalkoxy, aryl, arylalkyl and heterocyclyl groups are optionally substituted;
- wherein optional substitution is substitution with one or more groups selected from oxo, thiox, -sulfhydryl, hydroxy, alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, carbocyclyl, carbocyclyloxy, heterocyclyl, heterocyclyloxy, alkylthio, alkenylthio, alkynylthio, arylthio, thioheteroaryl, thiocarbocyclyl, thioheterocyclyl, —CORs, —COH, —OCORs, —OCOH, —CO—ORs, —CO—OH, —CO—O—CO-Rs, —CON(Rs)2, —CONHRs, —CONH2, —NRs-CORs, —NHCORs, —NHRs, —N(Rs)2, —O—SO2-Rs, —SO2-Rs, —SO2—NHRs, —SO2—N(Rs)2, —NRs-SO2-Rs, —NH—SO2-Rs, —NRsCO—N(Rs)2, —NH—CO—NHRs, —O—PO(ORs)2, —O—PO(ORs)(N(Rs)2), —O—PO(N(Rs)2)2, —N—PO(ORs)2, —N—PO(ORs)(N(Rs)2), —P(Rs)2, —B(OH)2, —B(OH)(ORs), and —B(ORs)2, where each Rs independently is an alkyl, alkenyl, alkynyl, aryl, heteroaryl, carbocyclyl, or heterocyclyl group or two Rs within the same substituent can together form a carbocyclic or heterocyclic ring having 3 to 10 ring atoms.
4 more elements
A compound of formula I:
- or salts thereof,
- where:
- R is hydrogen, an alkyl group, alkenyl group, or an alkynyl group;
- RA represents 1-3 non-hydrogen substituents on the ring;
- and
- RM is M or -L-M, where M is a polymer or a non-polymeric organic group, having from 1 to 100 carbon atoms and optionally nitrogen, oxygen or sulfur atoms, and -L is a divalent linker moiety having from 1-30 carbon atoms and optionally nitrogen, oxygen or sulfur atoms;
- wherein RA is an alkyl or alkoxy group substituted with a —CO—O—CO-Rs group, wherein Rs is an alkyl group;
- wherein RM is -L-M, where M is an alkyl, alkynyl, cycloalkyl, aryl, arylalkyl, heterocyclyl or heteroaryl group which is optionally substituted;
- and
- wherein optional substitution is substitution with one or more groups selected from oxo, thiox, halogen, nitro, cyano, cyanate, azido, thiocyano, isocyano, isothiocyano, sulfhydryl, hydroxy, alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, carbocyclyl, carbocyclyloxy, heterocyclyl, heterocyclyloxy, alkylthio, alkenylthio, alkynylthio, arylthio, thioheteroaryl, thiocarbocyclyl, thioheterocyclyl, —CORs, —COH, —OCORs, —OCOH, —CO—ORs, —CO—OH, —CO—O—CO-Rs, —CON(Rs)2, —CONHRs, —CONH2, —NRs-CORs, —NHCORs, —NHRs, —N(Rs)2, —O—SO2-Rs, —SO2-Rs, —SO2—NHRs, —SO2—N(Rs)2, —NRs-SO2-Rs, —NH—SO2-Rs, —NRsCO—N(Rs)2, —NH—CO—NHRs, —O—PO(ORs)2, —O—PO(ORs)(N(Rs)2), —O—PO(N(Rs)2)2, —N—PO(ORs)2, —N—PO(ORs)(N(Rs)2), —P(Rs)2, —B(OH)2, —B(OH)(ORs), and —B(ORs)2, where each Rs independently is an alkyl, alkenyl, alkynyl, aryl, heteroaryl, carbocyclyl, or heterocyclyl group or two Rs within the same substituent can together form a carbocyclic or heterocyclic ring having 3 to 10 ring atoms.
7 more elements
A compound of formula I:
- or salts thereof,
- where:
- R is hydrogen, or an alkyl group;
- RM is -L-M, where -L- is an alkylene linker having 1-6 carbon atoms and M is a 2-pyridyldithio group;
- wherein RA is an alkyl or alkoxy group substituted with a —CO—O—CO-Rs group, wherein Rs is an alkyl group.
2 more elements
Dependencies are inferred from the claim text.