Lacto-N-fucopentaose II

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 599112

CAS#: 21973-23-9

Description: Lacto-N-fucopentaose II is a ganglioside containing sialylated lacto-N-fucopentaose II is gastrointestinal cancer-asociated antigen detected by monoclonal antibody 19-9 in colorectal carcinoma cell line SW 1116.


Chemical Structure

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Lacto-N-fucopentaose II
CAS# 21973-23-9

Theoretical Analysis

MedKoo Cat#: 599112
Name: Lacto-N-fucopentaose II
CAS#: 21973-23-9
Chemical Formula: C32H55NO25
Exact Mass: 853.3063
Molecular Weight: 853.77
Elemental Analysis: C, 45.02; H, 6.49; N, 1.64; O, 46.85

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Lacto-N-fucopentaose II; Lnfp II; Lnfp-II; LnfpII;

IUPAC/Chemical Name: N-((2S,3R,4R,5S,6R)-2-(((2S,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-(((2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl)oxy)tetrahydro-2H-pyran-4-yl)oxy)-6-(hydroxymethyl)-4-(((2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-5-(((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-3-yl)acetamide

InChi Key: FKADDOYBRRMBPP-UOPSVCGPSA-N

InChi Code: InChI=1S/C32H55NO25/c1-8-16(42)20(46)22(48)30(51-8)56-26-14(7-38)54-29(15(33-9(2)39)27(26)57-31-23(49)21(47)18(44)12(5-36)52-31)58-28-19(45)13(6-37)53-32(24(28)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

SMILES Code: O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@@H]2[C@@H](CO)O[C@@H](O[C@@H]3[C@H]([C@H](O[C@@H]([C@H](O)[C@@H](O)C=O)[C@H](O)CO)O[C@H]([C@@H]3O)CO)O)[C@H](NC(C)=O)[C@H]2O[C@@H]4O[C@H](CO)[C@H](O)[C@H]([C@H]4O)O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

Preparing Stock Solutions

The following data is based on the product molecular weight 853.77 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: El-Hawiet A, Kitova EN, Klassen JS. Recognition of human milk oligosaccharides by bacterial exotoxins. Glycobiology. 2015 Aug;25(8):845-54. doi: 10.1093/glycob/cwv025. Epub 2015 May 4. PubMed PMID: 25941008.

2: Saumonneau A, Champion E, Peltier-Pain P, Molnar-Gabor D, Hendrickx J, Tran V, Hederos M, Dekany G, Tellier C. Design of an α-L-transfucosidase for the synthesis of fucosylated HMOs. Glycobiology. 2016 Mar;26(3):261-9. doi: 10.1093/glycob/cwv099. Epub 2015 Nov 17. PubMed PMID: 26582607.

3: Alderete TL, Autran C, Brekke BE, Knight R, Bode L, Goran MI, Fields DA. Associations between human milk oligosaccharides and infant body composition in the first 6 mo of life. Am J Clin Nutr. 2015 Dec;102(6):1381-8. doi: 10.3945/ajcn.115.115451. Epub 2015 Oct 28. PubMed PMID: 26511224.

4: Difilippo E, Pan F, Logtenberg M, Willems RH, Braber S, Fink-Gremmels J, Schols HA, Gruppen H. Milk Oligosaccharide Variation in Sow Milk and Milk Oligosaccharide Fermentation in Piglet Intestine. J Agric Food Chem. 2016 Mar 16;64(10):2087-93. doi: 10.1021/acs.jafc.6b00497. Epub 2016 Mar 1. PubMed PMID: 26882005.

5: Kuhn L, Kim HY, Hsiao L, Nissan C, Kankasa C, Mwiya M, Thea DM, Aldrovandi GM, Bode L. Oligosaccharide composition of breast milk influences survival of uninfected children born to HIV-infected mothers in Lusaka, Zambia. J Nutr. 2015 Jan;145(1):66-72. doi: 10.3945/jn.114.199794. Epub 2014 Nov 19. PubMed PMID: 25527660; PubMed Central PMCID: PMC4264023.

6: Rudloff S, Pohlentz G, Borsch C, Lentze MJ, Kunz C. Urinary excretion of in vivo ¹³C-labelled milk oligosaccharides in breastfed infants. Br J Nutr. 2012 Apr;107(7):957-63. doi: 10.1017/S0007114511004016. Epub 2011 Sep 5. PubMed PMID: 21888740.

7: Pirkl A, Soltwisch J, Draude F, Dreisewerd K. Infrared matrix-assisted laser desorption/ionization orthogonal-time-of-flight mass spectrometry employing a cooling stage and water ice as a matrix. Anal Chem. 2012 Jul 3;84(13):5669-76. doi: 10.1021/ac300840b. Epub 2012 Jun 12. PubMed PMID: 22670870.

8: Loveless RW, Feizi T, Childs RA, Mizuochi T, Stoll MS, Oldroyd RG, Lachmann PJ. Bovine serum conglutinin is a lectin which binds non-reducing terminal N-acetylglucosamine, mannose and fucose residues. Biochem J. 1989 Feb 15;258(1):109-13. PubMed PMID: 2649083; PubMed Central PMCID: PMC1138330.

9: Ko BJ, Brodbelt JS. Ultraviolet photodissociation of chromophore-labeled oligosaccharides via reductive amination and hydrazide conjugation. J Mass Spectrom. 2011 Apr;46(4):359-66. doi: 10.1002/jms.1901. PubMed PMID: 21438085.

10: Kogelberg H, Frenkiel TA, Homans SW, Lubineau A, Feizi T. Conformational studies on the selectin and natural killer cell receptor ligands sulfo- and sialyl-lacto-N-fucopentaoses (SuLNFPII and SLNFPII) using NMR spectroscopy and molecular dynamics simulations. Comparisons with the nonacidic parent molecule LNFPII. Biochemistry. 1996 Feb 13;35(6):1954-64. PubMed PMID: 8639679.

11: Bush CA, Panitch MM, Dua VK, Rohr TE. Carbon nuclear magnetic resonance spectra of oligosaccharides isolated from human milk and ovarian cyst mucin. Anal Biochem. 1985 Feb 15;145(1):124-36. PubMed PMID: 2988366.

12: Säwén E, Hinterholzinger F, Landersjö C, Widmalm G. Conformational flexibility of the pentasaccharide LNF-2 deduced from NMR spectroscopy and molecular dynamics simulations. Org Biomol Chem. 2012 Jun 21;10(23):4577-85. doi: 10.1039/c2ob25189b. Epub 2012 May 10. PubMed PMID: 22572908.

13: Chaturvedi P, Warren CD, Ruiz-Palacios GM, Pickering LK, Newburg DS. Milk oligosaccharide profiles by reversed-phase HPLC of their perbenzoylated derivatives. Anal Biochem. 1997 Aug 15;251(1):89-97. PubMed PMID: 9300087.

14: Larkin M, Ahern TJ, Stoll MS, Shaffer M, Sako D, O'Brien J, Yuen CT, Lawson AM, Childs RA, Barone KM, et al. Spectrum of sialylated and nonsialylated fuco-oligosaccharides bound by the endothelial-leukocyte adhesion molecule E-selectin. Dependence of the carbohydrate binding activity on E-selectin density. J Biol Chem. 1992 Jul 5;267(19):13661-8. Erratum in: J Biol Chem 1992 Aug 25;267(24):17478. PubMed PMID: 1377689.

15: Solouki T, Reinhold BB, Costello CE, O'Malley M, Guan S, Marshall AG. Electrospray ionization and matrix-assisted laser desorption/ionization Fourier transform ion cyclotron resonance mass spectrometry of permethylated oligosaccharides. Anal Chem. 1998 Mar 1;70(5):857-64. PubMed PMID: 9511464.

16: Alexander J, del Guercio MF, Maewal A, Qiao L, Fikes J, Chesnut RW, Paulson J, Bundle DR, DeFrees S, Sette A. Linear PADRE T helper epitope and carbohydrate B cell epitope conjugates induce specific high titer IgG antibody responses. J Immunol. 2000 Feb 1;164(3):1625-33. PubMed PMID: 10640784.

17: Xu Q, Gitti R, Bush CA. Comparison of NMR and molecular modeling results for a rigid and a flexible oligosaccharide. Glycobiology. 1996 Apr;6(3):281-8. PubMed PMID: 8724136.

18: Totten SM, Zivkovic AM, Wu S, Ngyuen U, Freeman SL, Ruhaak LR, Darboe MK, German JB, Prentice AM, Lebrilla CB. Comprehensive profiles of human milk oligosaccharides yield highly sensitive and specific markers for determining secretor status in lactating mothers. J Proteome Res. 2012 Dec 7;11(12):6124-33. doi: 10.1021/pr300769g. Epub 2012 Nov 19. PubMed PMID: 23140396.

19: Magnani JL. Carbohydrate differentiation and cancer-associated antigens detected by monoclonal antibodies. Biochem Soc Trans. 1984 Jun;12(3):543-5. PubMed PMID: 6588011.

20: Soltwisch J, Souady J, Berkenkamp S, Dreisewerd K. Effect of gas pressure and gas type on the fragmentation of peptide and oligosaccharide ions generated in an elevated pressure UV/IR-MALDI ion source coupled to an orthogonal time-of-flight mass spectrometer. Anal Chem. 2009 Apr 15;81(8):2921-34. doi: 10.1021/ac802301s. PubMed PMID: 19301914.