US 11,851,455 B2
Acidic dystroglycan oligosaccharide compound and method for making same
Xinyu Liu, Wexford, PA (US); and Aniruddha Sasmal, San Diego, CA (US)
Assigned to University of Pittsburgh Of The Commonwealth System of Higher Education, Pittsburgh, PA (US)
Appl. No. 16/960,271
Filed by UNIVERSITY OF PITTSBURGH - OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION, Pittsburgh, PA (US)
PCT Filed Jan. 7, 2019, PCT No. PCT/US2019/012577
§ 371(c)(1), (2) Date Dec. 10, 2020,
PCT Pub. No. WO2019/136399, PCT Pub. Date Jul. 11, 2019.
Claims priority of provisional application 62/614,173, filed on Jan. 5, 2018.
Prior Publication US 2022/0081463 A1, Mar. 17, 2022
Int. Cl. C07H 15/04 (2006.01)
CPC C07H 15/04 (2013.01) 5 Claims
 
1. A method for preparing a synthetic dystroglycan oligosaccharide comprising:

OG Complex Work Unit Chemistry
with a repeating disaccharide motif consists of Glucuronic Acid (GlcA) and Xylose (Xyl) having a defined glycosyl connection GlcA-β-(1→4)-Xyl-α-(1→3)-GlcA, comprising:
using a redox mediated one-pot intramolecular aglycon delivery (IAD) reaction comprising activating xylose thioglycoside with 2,3-Dichloro-5,6-dicyano-β-benzoquinone (DDQ) to produce a mixed acetal;
reacting the mixed acetal with tris-(4-bromophenyl) ammoniumyl hexachloroantimonate (BAHA), a single electron transfer reagent and 3-OH glucuronic acid acceptor to produce a 1,2-cis glycosylated product; and
using a base mediated deprotection method to remove protecting groups from the 1,2-cis glycosylated product to produce the synthetic dystroglycan oligosaccharide.