N-[(2R,3R,4R,5R)-5,6-dihydroxy-1-oxo-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyhexan-2-yl]acetamide

Modify Date: 2024-01-20 02:04:04

N-[(2R,3R,4R,5R)-5,6-dihydroxy-1-oxo-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyhexan-2-yl]acetamide structure	Common Name	N-[(2R,3R,4R,5R)-5,6-dihydroxy-1-oxo-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyhexan-2-yl]acetamide
	CAS Number	71208-06-5	Molecular Weight	529.49000
	Density	1.65g/cm3	Boiling Point	892.4ºC at 760 mmHg
	Molecular Formula	C₂₀H₃₅NO₁₅	Melting Point	155-156ºC
	MSDS	N/A	Flash Point	493.5ºC

Use of N-[(2R,3R,4R,5R)-5,6-dihydroxy-1-oxo-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyhexan-2-yl]acetamide

Lewis X trisaccharide (Lewis X, Lex) is a potent TH2 regulator, antagonizes LPS-induced IL-12 immune expression. Lewis X trisaccharide is a human histo-blood group antigen, plays an key role in cell-cell adhesion, and servers as a tumor marker. Lewis X trisaccharide is highly expressed in the outer membrane of the parasite, can be used for the immunology research of schistosomiasis[1][2][3].

Name	lewis x trisaccharide
Synonym	More Synonyms

Description	Lewis X trisaccharide (Lewis X, Lex) is a potent TH2 regulator, antagonizes LPS-induced IL-12 immune expression. Lewis X trisaccharide is a human histo-blood group antigen, plays an key role in cell-cell adhesion, and servers as a tumor marker. Lewis X trisaccharide is highly expressed in the outer membrane of the parasite, can be used for the immunology research of schistosomiasis[1][2][3].
Related Catalog	Research Areas >> Cancer Research Areas >> Infection Research Areas >> Inflammation/Immunology
In Vitro	Lewis X trisaccharide-BSA (25 μg/mL; 30 min; before LPS stimulation of 10 ng/mL for 4 h) IL-12p40 and suppresses IL-12p70 protein expression induced by Lipopolysaccharide (LPS, HY-D1056)[1]. Lewis X trisaccharide (2 μM; 30 min; before LPS stimulation of 10 ng/mL for 2 h) decreases nuclear NF-κB concentration in mice bone marrow derived dendritic cells (BDDCs)[1]. Lewis X trisaccharide-BSA (25 μg/mL; 48 h) or Lewis X trisaccharide (5 μg/mL; 48 h) plus ovalbumin (OVA, 25 μg/mL) increases cytokines (IL-4, IL-13, and INF-γ) level in mice splenocytes[1]. Lewis X trisaccharide-containing glycoconjugates stimulates B cells to proliferate and to produce factors that down-regulates the TH1 immune response and up-regulates the TH2 immune response[2].
In Vivo	Lewis X trisaccharide ( 5 μg, combinded with 50 μg ovalbumin; s.c.; once a week for 2 weeks) regulates IgE/TH2 responses, and selectively increases the IgE and IgG1 responses in C3H mice, independent of the LPS-TLR4 signaling[1]. Animal Model: Mice (BALB/c, IL-12 deficient on a BALB/c background, TLR4-defective C3H/hej, or TLR4-wild type C3H/HeOuj mice) (6-8 weeks old)[1] Dosage: 5 μg, combinded with 50 μg ovalbumin Administration: Subcutaneous injection; once a week for 2 weeks Result: In C3H mice, coupled with BSA (LeX-BSA) and elicited higher levels of specific IgE and IgG1, but not IgG2a, which were associated with increased levels of splenic TH2 cytokines when compared with those seen in BSA-sensitized mice. In BALB/c mice, induced by ovalbumin, significantly increased levels of specific IgE, resulted IgG2a antibodies concomitant with reduced levels of serum IL-12p70. In IL-12-deficient BALB/c mice, attenuated the downward trend of the above indicators.
References	[1]. Hsu SC, et al. Antigen coupled with Lewis-x trisaccharides elicits potent immune responses in mice. J Allergy Clin Immunol. 2007 Jun;119(6):1522-8. [2]. van Roon AM, et al. Structure of an anti-Lewis X Fab fragment in complex with its Lewis X antigen. Structure. 2004 Jul;12(7):1227-36. [3]. Topin J, et al. The Hidden Conformation of Lewis x, a Human Histo-Blood Group Antigen, Is a Determinant for Recognition by Pathogen Lectins. ACS Chem Biol. 2016 Jul 15;11(7):2011-20.

Density	1.65g/cm3
Boiling Point	892.4ºC at 760 mmHg
Melting Point	155-156ºC
Molecular Formula	C₂₀H₃₅NO₁₅
Molecular Weight	529.49000
Flash Point	493.5ºC
Exact Mass	529.20100
PSA	257.32000
Index of Refraction	1.632

WGK Germany	3

lewisx

lex

N-[(2R,3R,4R,5R)-5,6-dihydroxy-1-oxo-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyhexan-2-yl]acetamide

Use of N-[(2R,3R,4R,5R)-5,6-dihydroxy-1-oxo-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyhexan-2-yl]acetamide

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