US 11,655,267 B2
Oligosaccharide preparations and compositions
Manuela Baur, Möhlin (CH); Estel Canet-Martinez, Basel (CH); Ruediger Hainz, Binzen (DE); Ulrich Hoeller, Basel (CH); Lisa Ann Laprade, Dedham, MA (US); John Michael Geremia, Watertown, MD (US); and Ghislain Schyns, Waltham, MA (US)
Assigned to DSM IP ASSETS B.V., Heerlen (NL)
Appl. No. 17/292,119
Filed by DSM IP Assets B.V., Heerlen (NL)
PCT Filed Nov. 8, 2019, PCT No. PCT/US2019/060463
§ 371(c)(1), (2) Date May 7, 2021,
PCT Pub. No. WO2020/097458, PCT Pub. Date May 14, 2020.
Claims priority of provisional application 62/757,233, filed on Nov. 8, 2018.
Claims priority of provisional application 62/757,486, filed on Nov. 8, 2018.
Prior Publication US 2021/0395284 A1, Dec. 23, 2021
Int. Cl. C07H 1/00 (2006.01); C07H 3/06 (2006.01)
CPC C07H 1/00 (2013.01) [C07H 3/06 (2013.01)] 9 Claims
 
1. A method of manufacturing a synthetic oligosaccharide composition, the method comprising:
(a) heating an aqueous composition that comprises at least one feed sugar and a catalyst to a pre-determined temperature for a period of time sufficient to induce polymerization of said at least one feed sugar; to thereby produce a batch of a synthetic oligosaccharide preparation;
wherein said batch comprises at least 1 kg of said synthetic oligosaccharide preparation; and wherein said synthetic oligosaccharide preparation comprises at least n fractions of oligosaccharides each having a distinct degree of polymerization selected from 1 (DP1 fraction) to n (DPn fraction), wherein n is an integer greater than or equal to 3; and wherein each fraction of said synthetic oligosaccharide preparation comprises from about 0.5% to about 15% anhydro-subunit containing oligosaccharides by relative abundance as measured by mass spectrometry;
(b) measuring a level of said catalyst in the produced batch of the synthetic oligosaccharide preparation;
(c) determining whether the measured catalyst level in the produced batch is less than 1 wt. % corresponding to a pre-determined acceptance criterion; and
(d) formulating at least a portion of said batch of said synthetic oligosaccharide preparation only if the measured catalyst level in the produced batch meets said pre-determined acceptance criterion.