Lacto-N-fucopentaose I

Category	Enterovirus (EV)
CAS	7578-25-8
Description	Lacto-N-fucopentaose I (LNFPI) is a human milk oligosaccharide (HMO), possessing antiviral and antibacterial activity. Lacto-N-fucopentaose I can reduce capsid protein VP1 to block virus adsorption, promote CDK2 and reduce cyclin E to recover cell cycle S phase block. Lacto-N-fucopentaose I inhibits ROS production and Apoptosis in virus-infected cells. Lacto-N-fucopentaose I can also regulate intestinal microbiota to affect immune system development.

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Product Information

Synonyms	LNFP I; Fuc-a-1,2-Gal-b-1,3-GlcNAc-b-1,3-Gal-b-1,4-Glc; Blood group O(H) type I determinant; α-l-fuc(1→2)-β-d-gal-(1→3)-β-d-glcnac-(1→3)-β-d-gal-(1→4)-d-glc; O-6-Deoxy-α-L-galactopyranosyl-(1→2)-O-β-D-galactopyranosyl-(1→3)-O-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1→3)-O-β-D-galactopyranosyl-(1→4)-D-glucose; Lacto-N-fucopentose 1; Lacto-N-fucopentose I; LNF 1; LNF I
IUPAC Name	N-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxyoxan-4-yl]oxy-4-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Molecular Weight	853.77
Molecular Formula	C32H55NO25
Canonical SMILES	CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(OC(C3O)CO)OC4C(C(OC(C4O)OC(C(CO)O)C(C(C=O)O)O)CO)O)NC(=O)C)CO)O)O)O)O)O
InChI	InChI=1S/C32H55NO25/c1-8-16(42)21(47)23(49)30(51-8)58-28-22(48)18(44)12(5-36)54-32(28)56-26-15(33-9(2)39)29(52-13(6-37)19(26)45)57-27-20(46)14(7-38)53-31(24(27)50)55-25(11(41)4-35)17(43)10(40)3-34/h3,8,10-32,35-38,40-50H,4-7H2,1-2H3,(H,33,39)/t8-,10-,11+,12+,13+,14+,15+,16+,17+,18-,19+,20-,21+,22-,23-,24+,25+,26+,27-,28+,29-,30-,31-,32-/m0/s1
InChIKey	DTVXXTISAIGIBA-LDODJJGTSA-N
Boiling Point	1266.9±65.0°C at 760 mmHg
Purity	≥95%
Density	1.7±0.1 g/cm3
Solubility	Soluble in DMSO (10 mM)
Appearance	White to Off-white Powder
Storage	Store at 2-8°C
In Vitro	Lacto-N-fucopentaose I (25-3200 μg/mL;48 h) exhibits certain cytotoxicity at 3200 μg/mL but no toxic reaction below 1600 μg/mL. Lacto-N-fucopentaose I (25-1600 μg/mL; 14-18 h) can protect EV71-infected RD cells from death. Lacto-N-fucopentaose I (100-400 μg/mL; 16 h) decreases markedly mRNA levels of VP1 and ROS production in EV71-infected RD cells at 400 μg/mL; leads to the recovery of EV71-induced S phase arrest in RD cells. Lacto-N-fucopentaose I (100 and 200 μg/mL; 3 days) inhibits cell Apoptosis in Caenorhabditis elegans; significantly decreases the levels of Egl-1, Ced-3 and Ced-4 Lacto-N-fucopentaose I can reduce the abundance of Sphingobacterium, Stenotrophomonas and Achromobacter; can increase the abundance of Micromonospora, Vibrio, Acidibacter, Gaiella, Devosia, Steroidobacter, Variibacter, Dactylosporangium, RB41, Pir4_lineage, Pirellula, Haliangium, Roseiflexus, Pedomicrobium, and Bradyrhizobium.
PSA	423.46000
Target	Endogenous Metabolite; CDK; Reactive Oxygen Species; Apoptosis; Enterovirus;