US 12,441,761 B2
Conjugation reagents and methods using 1,2-cyclohexanediones
Robert C. James, San Diego, CA (US); Stephen Verespy, III, San Diego, CA (US); Eric Cunyu Zhou, San Diego, CA (US); Eric Okerberg, San Diego, CA (US); Kelsey Rose Schramma, San Diego, CA (US); and Fei Huang, San Diego, CA (US)
Assigned to Encodia, Inc., San Diego, CA (US)
Filed by Encodia, Inc., San Diego, CA (US)
Filed on Mar. 10, 2023, as Appl. No. 18/182,199.
Application 18/182,199 is a division of application No. 17/535,516, filed on Nov. 24, 2021, granted, now 11,639,366.
Application 17/535,516 is a continuation of application No. PCT/US2021/057144, filed on Oct. 28, 2021.
Claims priority of provisional application 63/108,282, filed on Oct. 30, 2020.
Prior Publication US 2023/0295222 A1, Sep. 21, 2023
Int. Cl. C07K 1/13 (2006.01); C07C 49/603 (2006.01); C07D 235/02 (2006.01); C07K 1/107 (2006.01); G01N 33/58 (2006.01); G01N 33/68 (2006.01)
CPC C07K 1/13 (2013.01) [C07C 49/603 (2013.01); C07D 235/02 (2013.01); C07K 1/1072 (2013.01); G01N 33/582 (2013.01); G01N 33/68 (2013.01)] 9 Claims
OG exemplary drawing
 
1. A composition comprising a peptide-polynucleotide conjugate, wherein a covalent linkage connecting a peptide and a polynucleotide of the peptide-polynucleotide conjugate comprises the following substructure (D):

OG Complex Work Unit Chemistry
or a tautomer thereof, wherein:
the dashed bond to Nuc represents where substructure (D) is covalently linked to the polynucleotide;
the dashed bond to Pep represents where substructure (D) is covalently linked to the peptide;
R4 is an optional substituent on the cyclopentyl ring, and
each R4 is independently selected from the group consisting of C1-2 alkyl, C1-2 alkoxy, C1-2 haloalkyl, —COOR, SO3R, halo, hydroxy, and C(O)NR2;
each R is independently H or C1-4 alkyl optionally substituted with up to three groups selected from the group consisting of halo, OH, C1-2 alkyl, C1-2 haloalkyl, C1-2 alkoxy, and carbonyl (oxo), or two R groups on one N are forming a 4-8 membered ring optionally containing an additional one or two heteroatoms selected from N, O and S as ring members and optionally substituted with one or two groups selected from halo, C1-2 alkyl, C1-2 haloalkyl, C1-2 alkoxy, hydroxy, and carbonyl (oxo); and n is 0, 1, 2 or 3.