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MedKoo Cat#: 412836 | Name: Chitohexaose

Description:

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

Chitohexaose is a biochemical

Chemical Structure

Chitohexaose
Chitohexaose
CAS#6734-92-5

Theoretical Analysis

MedKoo Cat#: 412836

Name: Chitohexaose

CAS#: 6734-92-5

Chemical Formula: C36H68N6O25

Exact Mass: 984.4234

Molecular Weight: 984.96

Elemental Analysis: C, 43.90; H, 6.96; N, 8.53; O, 40.61

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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Related CAS #
6734-92-5 (free) 38854-46-5 (acetyl)
Synonym
Chitohexaose
IUPAC/Chemical Name
(2R,3S,4R,5R,6R)-5-amino-6-(((2S,3R,4R,5S,6R)-3-amino-2-(((2S,3R,4R,5S,6R)-3-amino-4-(((2R,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-5-(((2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-6-((((2R,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol
InChi Key
BKESYGFNPLIPQF-GXRNKMMISA-N
InChi Code
InChI=1S/C36H68N6O25/c37-13-24(53)19(48)7(1-43)58-31(13)57-6-12-28(64-32-14(38)25(54)20(49)8(2-44)59-32)30(66-34-16(40)27(56)22(51)10(4-46)61-34)18(42)36(63-12)67-35-17(41)29(23(52)11(5-47)62-35)65-33-15(39)26(55)21(50)9(3-45)60-33/h7-36,43-56H,1-6,37-42H2/t7-,8-,9-,10-,11-,12-,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23-,24-,25-,26-,27-,28-,29-,30-,31-,32+,33+,34+,35+,36+/m1/s1
SMILES Code
N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC[C@H]2O[C@H]([C@@H]([C@H]([C@@H]2O[C@@H]3O[C@@H]([C@H]([C@@H]([C@H]3N)O)O)CO)O[C@@H]4O[C@@H]([C@H]([C@@H]([C@H]4N)O)O)CO)N)O[C@@H]5O[C@@H]([C@H]([C@@H]([C@H]5N)O[C@@H]6O[C@@H]([C@H]([C@@H]([C@H]6N)O)O)CO)O)CO)CO)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
>2 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 984.96 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: Das P, Panda SK, Agarwal B, Behera S, Ali SM, Pulse ME, Solomkin JS, Opal SM, Bhandari V, Acharya S. Novel Chitohexaose Analog Protects Young and Aged mice from CLP Induced Polymicrobial Sepsis. Sci Rep. 2019 Feb 27;9(1):2904. doi: 10.1038/s41598-019-38731-3. PMID: 30814582; PMCID: PMC6393422. 2: Li K, Xing R, Liu S, Qin Y, Li P. Access to N-Acetylated Chitohexaose with Well-Defined Degrees of Acetylation. Biomed Res Int. 2017;2017:2486515. doi: 10.1155/2017/2486515. Epub 2017 Jun 5. PMID: 28656139; PMCID: PMC5474546. 3: Barman PK, Mukherjee R, Prusty BK, Suklabaidya S, Senapati S, Ravindran B. Chitohexaose protects against acetaminophen-induced hepatotoxicity in mice. Cell Death Dis. 2016 May 12;7(5):e2224. doi: 10.1038/cddis.2016.131. PMID: 27171266; PMCID: PMC4917664. 4: Shi Q, George J, Krystel J, Zhang S, Lapointe SL, Stelinski LL, Stover E. Hexaacetyl-chitohexaose, a chitin-derived oligosaccharide, transiently activates citrus defenses and alters the feeding behavior of Asian citrus psyllid. Hortic Res. 2019 Jun 8;6:76. doi: 10.1038/s41438-019-0158-y. PMID: 31231534; PMCID: PMC6555843. 5: Poosala P, Ichinose H, Kitaoka T. Spatial Geometries of Self-Assembled Chitohexaose Monolayers Regulate Myoblast Fusion. Int J Mol Sci. 2016 May 6;17(5):686. doi: 10.3390/ijms17050686. PMID: 27164094; PMCID: PMC4881512. 6: Panda SK, Kumar S, Tupperwar NC, Vaidya T, George A, Rath S, Bal V, Ravindran B. Chitohexaose activates macrophages by alternate pathway through TLR4 and blocks endotoxemia. PLoS Pathog. 2012;8(5):e1002717. doi: 10.1371/journal.ppat.1002717. Epub 2012 May 24. PMID: 22654663; PMCID: PMC3359989. 7: Hatakeyama M, Nakada F, Ichinose H, Kitaoka T. Direct stimulation of cellular immune response via TLR2 signaling triggered by contact with hybrid glyco- biointerfaces composed of chitohexaose and cellohexaose. Colloids Surf B Biointerfaces. 2019 Mar 1;175:517-522. doi: 10.1016/j.colsurfb.2018.12.039. Epub 2018 Dec 13. PMID: 30576996. 8: van Straaten KE, Barends TR, Dijkstra BW, Thunnissen AM. Structure of Escherichia coli Lytic transglycosylase MltA with bound chitohexaose: implications for peptidoglycan binding and cleavage. J Biol Chem. 2007 Jul 20;282(29):21197-205. doi: 10.1074/jbc.M701818200. Epub 2007 May 14. PMID: 17502382. 9: Amornloetwattana R, Robinson RC, Soysa HSM, van den Berg B, Suginta W. Chitoporin from Serratia marcescens: recombinant expression, purification and crystallization. Acta Crystallogr F Struct Biol Commun. 2020 Nov 1;76(Pt 11):536-543. doi: 10.1107/S2053230X20013874. Epub 2020 Oct 29. PMID: 33135672; PMCID: PMC7605108. 10: Suzuki K, Mikami T, Okawa Y, Tokoro A, Suzuki S, Suzuki M. Antitumor effect of hexa-N-acetylchitohexaose and chitohexaose. Carbohydr Res. 1986 Aug 15;151:403-8. doi: 10.1016/s0008-6215(00)90359-8. PMID: 3768901.

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