Reagents and methods for esterification

Patent metadata

Field	Value
Publication number	US-9790483-B2
Application number	US-201615093510-A
Country	US
Kind code	B2
Filing date	Apr 7, 2016
Priority date	Apr 9, 2015
Publication date	Oct 17, 2017
Grant date	Oct 17, 2017

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, R A represents 1-5 substituents on the indicated phenyl ring and R M is an organic group, which 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 are 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.

First claim

We claim:

1. A compound of formula I:

or salts thereof,
where:
R is an alkyl, alkenyl, alkynyl group or hydrogen,
R A is an alkyl or alkoxy at the para position on the indicated phenyl ring, and
R M is an alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or arylalkyl group which is optionally substituted with one or more alkyl, alkoxy, aryl, alkylaryl, halogen, haloalkyl, or haloalkoxy groups.

2. The compound of claim 1 , wherein R M is an alkyl, alkenyl, alkynyl, phenyl or benzyl group.

3. The compound of claim 1 , wherein R A is an alkyl group having 1-6 carbon atoms in the para position on the phenyl ring.

4. The compound of claim 1 , wherein R A is a methyl group in the para position on the phenyl ring.

5. The compound of claim 1 , wherein R M is an alkyl group having 1-6 carbon atoms or an alkynyl group having 2-6 carbon atoms.

6. The compound of claim 5 , wherein R A is an alkyl group substituted at the para position on the phenyl ring.

7. The compound of claim 6 , wherein R is hydrogen or a methyl group.

8. The compound of claim 1 , wherein R M is an alkyl group having 1-6 carbon atoms.

9. The compound of claim 8 , wherein R A is an alkyl group substituted at the para-position of the phenyl ring.

10. The compound of claim 9 , wherein R is hydrogen or a methyl group.

11. The compound of claim 1 , wherein R A is a methyl group substituted at the para position of the phenyl ring.

12. The compound of claim 11 , wherein R and R M are methyl or ethyl groups.

13. The compound of claim 12 , wherein R and R M are both methyl groups.

14. The compound of claim 1 , wherein R M is an alkyl, or benzyl group.

15. The compound of claim 14 , wherein R is hydrogen, or an alkyl group.

16. The compound of claim 15 , wherein R A is an alkyl group at the para position of the phenyl ring.

17. The compound of claim 15 , wherein R A is a methyl group at the para position of the phenyl ring.

Assignees

• Wisconsin Alumni Res Found

Inventors

• Raines Ronald T
• Mix Kalie

Classifications

• C07D207/46

  with hetero atoms directly attached to the ring nitrogen atom · CPC title

• C12N9/96 Primary

  Stabilising an enzyme by forming an adduct or a composition; Forming enzyme conjugates · CPC title

• C07K1/13

  Labelling of peptides · CPC title

• C07C269/06

  by reactions not involving the formation of carbamate groups · CPC title

• C07C245/18

  the carbon skeleton being further substituted by carboxyl groups · CPC title