6'-Sialyllactose

Catalog	BBC157574760
CAS	157574-76-0
Synonyms	Neu5Acα2, 6Galβ1, 4Glc
IUPAC Name	sodium;(2R,4S,5R,6R)-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]-2-[[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxyoxan-2-yl]methoxy]oxane-2-carboxylate
Molecular Weight	655.53
Molecular Formula	C23H38NNaO19
Canonical SMILES	CC(=O)N[C@@H]1[C@H](C[C@@](O[C@H]1[C@@H]([C@@H](CO)O)O)(C(=O)[O-])OC[C@@H]2[C@@H]([C@@H]([C@H]([C@@H](O2)O[C@H]([C@@H](CO)O)[C@@H]([C@H](C=O)O)O)O)O)O)O.[Na+]
InChI	InChI=1S/C23H39NO19.Na/c1-7(28)24-13-8(29)2-23(22(38)39,43-20(13)15(34)10(31)4-26)40-6-12-16(35)17(36)18(37)21(41-12)42-19(11(32)5-27)14(33)9(30)3-25;/h3,8-21,26-27,29-37H,2,4-6H2,1H3,(H,24,28)(H,38,39);/q;+1/p-1/t8-,9-,10+,11+,12+,13+,14+,15+,16-,17-,18+,19+,20+,21-,23+;/m0./s1
InChI Key	LJNVKOGOHXWREM-MZZLGFSDSA-M
Melting Point	177-179 °C
Purity	98%
Appearance	White to off-white solid
Solubility in Water	Sparingly

Case Study

6'-Sialyllactose Used for The C-Glycosidation

Johnson, S., et al. The Journal of organic chemistry 83.8 (2018): 4581-4597.

C-glycoside derivatives are prevalent in pharmaceuticals, glycoconjugates, probes, and other functional molecules, making the C-glycosidation of unprotected carbohydrates of significant interest. This study reports the development of C-glycosidation reactions involving unprotected di- and trisaccharide aldopyranoses with various ketones. The reactions were carried out using a catalyst system composed of pyrrolidine and boric acid under mild conditions. The carbohydrates used in the C-glycosidation include lactose, maltose, cellobiose, 3'-sialyllactose, 6'-sialyllactose, and maltotriose. By reacting these carbohydrates with functionalized ketones, C-glycosidic ketones containing the desired functional groups were obtained.
C-Glycosidation of Trisaccharide Aldopyranoses
The reactions of trisaccharide aldopyranoses were conducted using the pyrrolidine-boric acid catalysis system. Under these conditions, reactions of 3'-sialyllactose (6a), 6'-sialyllactose (6b), and maltotriose (6c) with ketones produced the corresponding C-glycoside products (7). Ketones such as acetone, alkyl methyl ketones containing various functional groups, ketones with a cyclopropane ring, and aryl methyl ketones all yielded the desired C-glycoside ketones. The use of the pyrrolidine-boric acid catalyst system enabled efficient C-glycosidation reactions of highly functionalized carbohydrates, including those bearing N-acetylneuraminic acid.

Synthesis of 3'-Sialyllactose- and 6'-Sialyllactose-Conjugated Dendritic Polymers

Günther, Sira Carolin, et al. Scientific reports 10.1 (2020): 768.

Given the limited treatment options for influenza virus infections, the development of new antiviral agents is a high priority. Inhibiting the attachment of the influenza virus to host cells provides an early and effective method of blocking the infection. As such, receptor analogs are being explored as potential antiviral treatments. This study presents the rapid and efficient synthesis of PAMAM dendrimers conjugated with either 3'-sialyllactose (3SL) or 6'-sialyllactose (6SL) and evaluates their potential to inhibit a range of human and avian influenza virus strains.
Inhibitor Synthesis:
Lactose and the trisaccharides 3SL and 6SL were first derivatized at their reducing end to form cyclic carbamates. This modification facilitated the efficient conjugation of these saccharides to primary amines in the PAMAM dendrimer backbone. The cyclic carbamate-derivatized lactose, 3SL, or 6SL (in excess of 2-3 molar equivalents per amino group of PAMAM) were reacted with commercial PAMAM dendrimers for several hours at ambient temperature in water. The resulting fully derivatized dendrimers (Lactose-PAMAM, (3SL)₄-PAMAM, (6SL)₄-PAMAM, (3SL)₈-PAMAM and (6SL)₈-PAMAM were purified using ion-exchange chromatography (Lactose-PAMAM on Dowex-50WXH⁺ and (6SL)₄-PAMAM on Dowex-1×4-HCO₃^-) followed by freeze-drying. However, the most efficient and straightforward isolation method was direct precipitation with methanol. All glycodendrimers were effectively precipitated by slowly adding the reaction mixture dropwise into stirring methanol.