US 12,378,328 B2
Biohybrid peptidoglycan oligomers
Xuewei Liu, Singapore (SG); Bee Eng Mary Chan, Singapore (SG); Hongwei Duan, Singapore (SG); Jingxi He, Singapore (SG); Kim Le Mai Hoang, Singapore (SG); and Liang Yang, Singapore (SG)
Assigned to Nanyang Technological University, Singapore (SG); and National University of Singapore, Singapore (SG)
Appl. No. 17/267,271
Filed by Nanyang Technological University, Singapore (SG); and National University of Singapore, Singapore (SG)
PCT Filed Sep. 19, 2019, PCT No. PCT/SG2019/050473
§ 371(c)(1), (2) Date Feb. 9, 2021,
PCT Pub. No. WO2020/060491, PCT Pub. Date Mar. 26, 2020.
Claims priority of application No. 10201808123Y (SG), filed on Sep. 18, 2019.
Prior Publication US 2022/0213232 A1, Jul. 7, 2022
Int. Cl. C08B 37/00 (2006.01); A61K 47/54 (2017.01); A61K 47/61 (2017.01); A61K 47/64 (2017.01); A61P 31/04 (2006.01); C08B 37/08 (2006.01); C12Q 1/18 (2006.01)
CPC C08B 37/003 (2013.01) [A61K 47/542 (2017.08); A61K 47/61 (2017.08); A61K 47/64 (2017.08); A61P 31/04 (2018.01); C12Q 1/18 (2013.01)] 20 Claims
 
1. A compound of formula Ia and/or formula Ib:

OG Complex Work Unit Chemistry
wherein:
R1 represents C1 to C20 alkyl or —CH2CH(CO2H)OC1-20 alkyl;
R2 and R3 each independently represent —C(═O)R7;
R4 to R6 each represent H;
each R7 independently represents C1 to C20 alkyl;
X1 and X2 independently represent -AA1-AA2-AA3-D-Ala-AA4, where:
AA1 is selected from L-Ala, L-Gly, D-Gly or L-Ser;
AA2 is selected from D-isoglutamate (γ-D-glutamate, γ-D-Glu), D-isoglutamine, or threo-3-hydroxyglutamate;
AA3 is selected from L-homoserine, D-homoserine, D-5-hydroxylysine, D-Orn, L-Lys, D-Lys, L-Orn, L-2,4-diaminobutyrate, or L-5-hydroxylysine, where the amino group is functionalised to become a NHR8 group and/or, where present, the hydroxyl group is functionalised to become a OR8 group; and
AA4 is selected from D-Ala, D-Ser or D-Lacate (D-Lac),
at each occurrence R8 is independently selected from one or more of H, a fluorescent group or a pharmaceutically active moiety,
n and m, and n′ and m′ are alternating repeating units, where n is from 5 to 100 and m is from 4 to 100, provided that m has the same value as n or is n−1 and n′ is from 5 to 100 and m′ is from 4 to 100, provided that m′ has the same value as n′ or is n′−1,
p or p′ are 1 or 0, or
a pharmaceutically acceptable salt, solvate or prodrug thereof.