Tyvelose | CAS#5658-12-8

MedKoo Cat#: 462795 | Name: Tyvelose

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Description:

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

Tyvelose is an unusual 3,6-dideoxyhexose terminal sugar and the immunodominant component of glycoprotein antigens in the parasitic helminth T. spiralis, which is responsible for trichinosis in humans. It is produced in high amounts by the infective larva and is immunodominant during the muscle stage of infection. Mice immunized with tyvelose-BSA produce IgG1 antibodies to tyvelose but are not resistant to infection by T. spiralis. Tyvelose-specific antibodies administered to rat pups leads to expulsion of first stage larvae from the intestine within one hour.

Chemical Structure

Tyvelose

CAS#5658-12-8

Theoretical Analysis

MedKoo Cat#: 462795

Name: Tyvelose

CAS#: 5658-12-8

Chemical Formula: C6H12O4

Exact Mass: 148.0736

Molecular Weight: 148.16

Elemental Analysis: C, 48.64; H, 8.16; O, 43.19

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 Weeks
10mg	USD 600.00	2 Weeks

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Related CAS #

No Data

Synonym

Dideoxyhexose; D-Tyvelose;

IUPAC/Chemical Name

(2S,4R,5R)-2,4,5-trihydroxyhexanal

InChi Key

GNTQICZXQYZQNE-NGJCXOISSA-N

InChi Code

InChI=1S/C6H12O4/c1-4(8)6(10)2-5(9)3-7/h3-6,8-10H,2H2,1H3/t4-,5+,6-/m1/s1

SMILES Code

C[C@H]([C@@H](C[C@@H](C=O)O)O)O

Appearance

Solid powder

Purity

>95% (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

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Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 148.16 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.

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: Podvalnyy NM, Crone L, Paganini D, Zimmermann MB, Hennet T. Synthesis of trisaccharide antigens featuring colitose, abequose and fucose residues and assessment of antibody binding on antigen arrays. Carbohydr Res. 2024 Nov;545:109283. doi: 10.1016/j.carres.2024.109283. Epub 2024 Sep 26. PMID: 39342778. 2: Vogel U, Da Costa M, Alvarez Quispe C, Stragier R, Joosten HJ, Beerens K, Desmet T. The Conversion of UDP-Glc to UDP-Man: In Silico and Biochemical Exploration To Improve the Catalytic Efficiency of CDP-Tyvelose C2-Epimerases. Chembiochem. 2023 Dec 1;24(23):e202300549. doi: 10.1002/cbic.202300549. Epub 2023 Oct 12. PMID: 37728070. 3: Yang S, Chu CJ, Lowary TL. A De Novo Route to 3,6-Dideoxy Sugars. Org Lett. 2022 Aug 5;24(30):5614-5618. doi: 10.1021/acs.orglett.2c02349. Epub 2022 Jul 26. PMID: 35880961. 4: Bunte MJM, Schots A, Kammenga JE, Wilbers RHP. Helminth Glycans at the Host- Parasite Interface and Their Potential for Developing Novel Therapeutics. Front Mol Biosci. 2022 Jan 10;8:807821. doi: 10.3389/fmolb.2021.807821. PMID: 35083280; PMCID: PMC8784694. 5: Soulier A, Prevosto C, Chol M, Deban L, Cranenburgh RM. Engineering a Novel Bivalent Oral Vaccine against Enteric Fever. Int J Mol Sci. 2021 Mar 23;22(6):3287. doi: 10.3390/ijms22063287. PMID: 33807097; PMCID: PMC8005139. 6: Liu MA, Kidambi A, Reeves PR. The low level of O antigen in Salmonella enterica Paratyphi A is due to inefficiency of the glycosyltransferase WbaV. FEMS Microbiol Lett. 2021 Feb 12;368(3):fnab009. doi: 10.1093/femsle/fnab009. PMID: 33476372. 7: Rapp C, van Overtveldt S, Beerens K, Weber H, Desmet T, Nidetzky B. Expanding the Enzyme Repertoire for Sugar Nucleotide Epimerization: The CDP-Tyvelose 2-Epimerase from Thermodesulfatator atlanticus for Glucose/Mannose Interconversion. Appl Environ Microbiol. 2021 Mar 1;87(4):e02131-20. doi: 10.1128/AEM.02131-20. Epub 2020 Dec 4. PMID: 33277270; PMCID: PMC7851689. 8: Ricci V, Zhang D, Teale C, Piddock LJV. The O-Antigen Epitope Governs Susceptibility to Colistin in Salmonella enterica. mBio. 2020 Jan 28;11(1):e02831-19. doi: 10.1128/mBio.02831-19. PMID: 31992619; PMCID: PMC6989106. 9: von Reuss SH. Exploring Modular Glycolipids Involved in Nematode Chemical Communication. Chimia (Aarau). 2018 May 30;72(5):297-303. doi: 10.2533/chimia.2018.297. PMID: 29789066. 10: Panczyk K, Plazinski W. Pyranose ring puckering in aldopentoses, ketohexoses and deoxyaldohexoses. A molecular dynamics study. Carbohydr Res. 2018 Jan 2;455:62-70. doi: 10.1016/j.carres.2017.11.011. Epub 2017 Nov 21. PMID: 29175656. 11: Sizova OV, Kondakova AN, Shashkov AS, Knirel YA, Shaikhutdinova RZ, Ivanov SA, Platonov ME, Hurst MRH, Dentovskaya SV. Structure and gene cluster of a tyvelose-containing O-polysaccharide of an entomopathogenic bacterium Yersinia entomophaga MH96T related to Yersinia pseudotuberculosis. Carbohydr Res. 2017 Jun 5;445:93-97. doi: 10.1016/j.carres.2017.04.013. Epub 2017 Apr 15. PMID: 28460348. 12: Panda O, Akagi AE, Artyukhin AB, Judkins JC, Le HH, Mahanti P, Cohen SM, Sternberg PW, Schroeder FC. Biosynthesis of Modular Ascarosides in C. elegans. Angew Chem Int Ed Engl. 2017 Apr 18;56(17):4729-4733. doi: 10.1002/anie.201700103. Epub 2017 Mar 28. PMID: 28371259; PMCID: PMC5486983. 13: Jaiswal S, Pati NB, Dubey M, Padhi C, Sahoo PK, Ray S, Arunima A, Mohakud NK, Suar M. The O-antigen negative ∆wbaV mutant of Salmonella enterica serovar Enteritidis shows adaptive resistance to antimicrobial peptides and elicits colitis in streptomycin pretreated mouse model. Gut Pathog. 2015 Sep 3;7:24. doi: 10.1186/s13099-015-0070-4. PMID: 26346801; PMCID: PMC4559907. 14: Ovchinnikova OG, Moryl M, Shashkov AS, Chizhov AO, Arbatsky NP, Shpirt AM, Rozalski A, Knirel YA. Structure of the O-polysaccharide of Providencia alcalifaciens O2 containing ascarylose and N-(L-alanyl)-D-glucosamine. Carbohydr Res. 2015 Jan 12;401:11-5. doi: 10.1016/j.carres.2014.10.016. Epub 2014 Oct 27. PMID: 25464076. 15: Cui L, Ling CC, Sadowska J, Bundle DR. Synthesis of modified Trichinella spiralis disaccharide epitopes and a comparison of their recognition by chemical mapping and saturation transfer difference NMR. Carbohydr Res. 2014 Jan 13;383:1-13. doi: 10.1016/j.carres.2013.10.012. Epub 2013 Nov 1. PMID: 24239604. 16: Zhang X, Noguez JH, Zhou Y, Butcher RA. Analysis of ascarosides from Caenorhabditis elegans using mass spectrometry and NMR spectroscopy. Methods Mol Biol. 2013;1068:71-92. doi: 10.1007/978-1-62703-619-1_6. PMID: 24014355; PMCID: PMC3947767. 17: Blum LK, Mohanan S, Fabre MV, Yafawi RE, Appleton JA. Intestinal infection with Trichinella spiralis induces distinct, regional immune responses. Vet Parasitol. 2013 May 20;194(2-4):101-5. doi: 10.1016/j.vetpar.2013.01.030. Epub 2013 Feb 5. PMID: 23465441; PMCID: PMC3655129. 18: Ludewig AH, Schroeder FC. Ascaroside signaling in C. elegans. WormBook. 2013 Jan 18:1-22. doi: 10.1895/wormbook.1.155.1. PMID: 23355522; PMCID: PMC3758900. 19: Andres D, Gohlke U, Broeker NK, Schulze S, Rabsch W, Heinemann U, Barbirz S, Seckler R. An essential serotype recognition pocket on phage P22 tailspike protein forces Salmonella enterica serovar Paratyphi A O-antigen fragments to bind as nonsolution conformers. Glycobiology. 2013 Apr;23(4):486-94. doi: 10.1093/glycob/cws224. Epub 2013 Jan 3. PMID: 23292517. 20: Tundup S, Srivastava L, Harn DA Jr. Polarization of host immune responses by helminth-expressed glycans. Ann N Y Acad Sci. 2012 Apr;1253:E1-E13. doi: 10.1111/j.1749-6632.2012.06618.x. PMID: 22974465.