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MedKoo Cat#: 584966 | Name: Globotriose

Description:

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

Globotriose is a triose composed of two galactose residues and one glucose residue involved in pathogenic processes and drug development strategies.

Chemical Structure

Globotriose
Globotriose
CAS#66580-68-5

Theoretical Analysis

MedKoo Cat#: 584966

Name: Globotriose

CAS#: 66580-68-5

Chemical Formula: C18H32O16

Exact Mass: 504.1690

Molecular Weight: 504.44

Elemental Analysis: C, 42.86; H, 6.39; O, 50.75

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Synonym
Globotriose; Gal-1-4-gal-1-4-glc; P(k) Trisaccharide
IUPAC/Chemical Name
4-O-(4-O-α-D-Galactopyranosyl-beta-D-galactopyranosyl)-D-glucopyranose
InChi Key
FYGDTMLNYKFZSV-ANKSBSNASA-N
InChi Code
InChI=1S/C18H32O16/c19-1-4-7(22)8(23)12(27)17(31-4)34-15-6(3-21)32-18(13(28)10(15)25)33-14-5(2-20)30-16(29)11(26)9(14)24/h4-29H,1-3H2/t4-,5-,6-,7+,8+,9-,10-,11-,12-,13-,14-,15+,16?,17-,18+/m1/s1
SMILES Code
OC1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O[C@H]2[C@@H]([C@H]([C@H]([C@@H](CO)O2)O[C@@H]3[C@@H]([C@H]([C@H]([C@@H](CO)O3)O)O)O)O)O)O)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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 504.44 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
1: Zhao X, Zou Y, Xue M, Ma Z, Wang S, Wang PG, Chen M. A one-pot approach to bio-synthesize globotriose and its derivatives from simpler substrates. Eur J Med Chem. 2014 Jun 10;80:423-7. doi: 10.1016/j.ejmech.2014.04.067. Epub 2014 Apr 24. PubMed PMID: 24796882. 2: Pandey B, Tan YH, Parameswar AR, Pornsuriyasak P, Demchenko AV, Stine KJ. Electrochemical characterization of globotriose-containing self-assembled monolayers on nanoporous gold and their binding of soybean agglutinin. Carbohydr Res. 2013 May 24;373:9-17. doi: 10.1016/j.carres.2012.09.021. Epub 2012 Oct 13. PubMed PMID: 23545324; PubMed Central PMCID: PMC3615452. 3: Liao JH, Chien CT, Wu HY, Huang KF, Wang I, Ho MR, Tu IF, Lee IM, Li W, Shih YL, Wu CY, Lukyanov PA, Hsu ST, Wu SH. A Multivalent Marine Lectin from Crenomytilus grayanus Possesses Anti-cancer Activity through Recognizing Globotriose Gb3. J Am Chem Soc. 2016 Apr 13;138(14):4787-95. doi: 10.1021/jacs.6b00111. Epub 2016 Apr 1. PubMed PMID: 27010847. 4: Gong W, Xu L, Gu G, Lu L, Xiao M. Efficient and regioselective synthesis of globotriose by a novel α-galactosidase from Bacteroides fragilis. Appl Microbiol Biotechnol. 2016 Aug;100(15):6693-6702. doi: 10.1007/s00253-016-7464-1. Epub 2016 Mar 28. PubMed PMID: 27020280. 5: Leach JL, Garber SA, Marcon AA, Prieto PA. In vitro and in vivo effects of soluble, monovalent globotriose on bacterial attachment and colonization. Antimicrob Agents Chemother. 2005 Sep;49(9):3842-6. PubMed PMID: 16127061; PubMed Central PMCID: PMC1195436. 6: Paton AW, Morona R, Paton JC. Neutralization of Shiga toxins Stx1, Stx2c, and Stx2e by recombinant bacteria expressing mimics of globotriose and globotetraose. Infect Immun. 2001 Mar;69(3):1967-70. PubMed PMID: 11179385; PubMed Central PMCID: PMC98114. 7: Watanabe M, Igai K, Matsuoka K, Miyagawa A, Watanabe T, Yanoshita R, Samejima Y, Terunuma D, Natori Y, Nishikawa K. Structural analysis of the interaction between Shiga toxin B subunits and linear polymers bearing clustered globotriose residues. Infect Immun. 2006 Mar;74(3):1984-8. PubMed PMID: 16495579; PubMed Central PMCID: PMC1418665. 8: Antoine T, Bosso C, Heyraud A, Samain E. Large scale in vivo synthesis of globotriose and globotetraose by high cell density culture of metabolically engineered Escherichia coli. Biochimie. 2005 Feb;87(2):197-203. PubMed PMID: 15760713. 9: Watanabe M, Matsuoka K, Kita E, Igai K, Higashi N, Miyagawa A, Watanabe T, Yanoshita R, Samejima Y, Terunuma D, Natori Y, Nishikawa K. Oral therapeutic agents with highly clustered globotriose for treatment of Shiga toxigenic Escherichia coli infections. J Infect Dis. 2004 Feb 1;189(3):360-8. Epub 2004 Jan 21. PubMed PMID: 14745692. 10: Okochi A, Tanimoto S, Takahashi D, Toshima K. Target-selective photo-degradation of verotoxin-1 and reduction of its cytotoxicity to Vero cells using porphyrin-globotriose hybrids. Chem Commun (Camb). 2013 Jul 11;49(54):6027-9. doi: 10.1039/c3cc42957a. PubMed PMID: 23722161. 11: Blomberg E, Claesson PM, Konradsson P, Liedberg B. Globotriose- and oligo(ethylene glycol)-terminated self-assembled monolayers: surface forces, wetting, and surfactant adsorption. Langmuir. 2006 Nov 21;22(24):10038-46. PubMed PMID: 17106997. 12: Ghosh S, Andreana PR. Synthesis of an Aminooxy Derivative of the Trisaccharide Globotriose Gb3. J Carbohydr Chem. 2014 Sep 1;33(7-8):381-394. PubMed PMID: 25382930; PubMed Central PMCID: PMC4219983. 13: Koizumi S, Endo T, Tabata K, Ozaki A. Large-scale production of UDP-galactose and globotriose by coupling metabolically engineered bacteria. Nat Biotechnol. 1998 Sep;16(9):847-50. PubMed PMID: 9743118. 14: Masoud H, Martin A, Thibault P, Moxon ER, Richards JC. Structure of extended lipopolysaccharide glycoforms containing two globotriose units in Haemophilus influenzae serotype b strain RM7004. Biochemistry. 2003 Apr 22;42(15):4463-75. PubMed PMID: 12693942. 15: Li X, Wu P, Cheng S, Lv X. Synthesis and assessment of globotriose-chitosan conjugate, a novel inhibitor of shiga toxins produced by Escherichia coli. J Med Chem. 2012 Mar 22;55(6):2702-10. doi: 10.1021/jm201570s. Epub 2012 Mar 8. PubMed PMID: 22372889. 16: Chen L, Zhao XE, Lai D, Song Z, Kong F. A concise and practical synthesis of antigenic globotriose, alpha-D-Gal-(1-->4)-beta-D-Gal-(1-->4)-beta-D-Glc. Carbohydr Res. 2006 Jul 3;341(9):1174-80. Epub 2006 Apr 21. PubMed PMID: 16630600. 17: Skinner C, McMahon S, Rasooly R, Carter JM, He X. Purification and characterization of Shiga toxin 2f, an immunologically unrelated subtype of Shiga toxin 2. PLoS One. 2013;8(3):e59760. doi: 10.1371/journal.pone.0059760. Epub 2013 Mar 26. PubMed PMID: 23555772; PubMed Central PMCID: PMC3608586. 18: Volynsky P, Efremov R, Mikhalev I, Dobrochaeva K, Tuzikov A, Korchagina E, Obukhova P, Rapoport E, Bovin N. Why human anti-Galα1-4Galβ1-4Glc natural antibodies do not recognize the trisaccharide on erythrocyte membrane? Molecular dynamics and immunochemical investigation. Mol Immunol. 2017 Oct;90:87-97. doi: 10.1016/j.molimm.2017.06.247. Epub 2017 Jul 11. PubMed PMID: 28708979. 19: Hansen HC, Magnusson G. Synthesis of some divalent O- and S-glycosides of galabiose and globotriose. Carbohydr Res. 1998 Feb;307(3-4):243-51. PubMed PMID: 9675366. 20: Liu MZ, Fan HN, Lee YC. Chemical synthesis of a P(k)-antigenic globotriose analogue with a functionalized aglycon. Biochimie. 2001 Jul;83(7):693-8. PubMed PMID: 11522399.

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