	US 7,399,645 B2
	Constrained cis-diol-borate bioconjugation system
Ricky F. Baggio, Waltham, Mass. (US); Alison L. Sparks, North Andover, Mass. (US); Rouh-Rong Juo, Allston, Mass. (US); and Jaime E. Arenas, Lexington, Mass. (US)
Assigned to Applera Corporation, Bedford, Mass. (US)
Filed on May 11, 2005, as Appl. No. 11/126,837.
Claims priority of provisional application 60/570313, filed on May 12, 2004.
Claims priority of provisional application 60/578946, filed on Jun. 10, 2004.
Prior Publication US 2005/0277143 A1, Dec. 15, 2005
Int. Cl. G01N 33/547 (2006.01); G01N 33/543 (2006.01); G01N 33/532 (2006.01); C07K 1/10 (2006.01); C07K 1/13 (2006.01); C07F 5/02 (2006.01)

U.S. Cl. 436—532 [436/518; 436/543; 530/402; 530/403; 530/406; 530/812; 568/1]

44 Claims

1. A bioconjugation system, comprising a sterically constrained cis-diol and a borate represented respectively by:

wherein:

R¹is C2-C16 alkyl ether, C1-C16 alkoxy or C1-C16 alkyl;

R¹is an aryl, aralkyl, C1-C16 alkyl, or C1-C16 alkoxy group;

wherein the cis-diol and borate are bonded through the hydroxyl groups to form a conjugate represented by:

X is —NH—, —C(O)NH—, —NHC(O)— or —S—;

X′ is a bond, —O—, —S—, —C(O)—, —C(O)O—, —S(O)—, —OSO₂—, —S(O₂)O—, —SO₂—, —NR³—, —NR³C(O)—, —C(O)NR³C—, —R³NNR³SO₂—, —SO₂NR³NR³—, —NR³SO₂—, —SO₂NR³—, —CR³₂C(O)NR³—, —NR³C(O)CR³₂, —CR³₂C(O)—, —C(O)CR³₂—, —R³NNR³—, —NR³NR³—, —R³NNR³₂—, —NR³₂NR³—, —CR³₂Ph—, —PhCR³₂—, —C(NR³)NR³—, or —NR³C(NR³)—;

each R³is independently —H, alkyl, alkoxy, aryloxy or arylalkoxy;

Y is a solid support;

Y′ is a bioactive molecule comprising one or more peptides;

n is an integer from 10 to 10¹⁰; and

n′ is an integer from 1 to 200.