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MedKoo Cat#: 561186 | Name: Conduritol B epoxide
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Description:

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

Conduritol B epoxide, also known as CBE, is an inhibitor of non-mammalian and mammalian β-glucosidase. When injected in mice it produces the biochemical and certain clinical and pathological characteristics of Gaucher disease. Conduritol B epoxide is a mechanism-based inhibitor which binds covalently to the catalytic site of acid β-glucosidase.

Chemical Structure

Conduritol B epoxide
Conduritol B epoxide
CAS#6090-95-5

Theoretical Analysis

MedKoo Cat#: 561186

Name: Conduritol B epoxide

CAS#: 6090-95-5

Chemical Formula: C6H10O5

Exact Mass: 162.0528

Molecular Weight: 162.14

Elemental Analysis: C, 44.45; H, 6.22; O, 49.34

Price and Availability

Size Price Availability Quantity
5mg USD 195.00 2 weeks
25mg USD 415.00 2 weeks
50mg USD 760.00 2 weeks
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Related CAS #
No Data
Synonym
Conduritol B epoxide; Conduritol-B-epoxide; CBE
IUPAC/Chemical Name
(1R,2R,3S,4S,5R,6S)-7-oxabicyclo[4.1.0]heptane-2,3,4,5-tetrol
InChi Key
ZHMWOVGZCINIHW-FTYOSCRSSA-N
InChi Code
InChI=1S/C6H10O5/c7-1-2(8)4(10)6-5(11-6)3(1)9/h1-10H/t1-,2-,3+,4+,5-,6+/m0/s1
SMILES Code
O[C@H]1[C@@]2([H])O[C@@]2([H])[C@H](O)[C@@H](O)[C@@H]1O
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
Certificate of Analysis
View CoA: current batch, Lot#A24M03B18
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 162.14 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: Lee KJ, Boyd SA, Radin NS. Improved synthesis of conduritol B epoxide. Carbohydr Res. 1985 Nov 15;144(1):148-54. doi: 10.1016/0008-6215(85)85015-1. PMID: 4075334. 2: Kuo CL, Kallemeijn WW, Lelieveld LT, Mirzaian M, Zoutendijk I, Vardi A, Futerman AH, Meijer AH, Spaink HP, Overkleeft HS, Aerts JMFG, Artola M. In vivo inactivation of glycosidases by conduritol B epoxide and cyclophellitol as revealed by activity-based protein profiling. FEBS J. 2019 Feb;286(3):584-600. doi: 10.1111/febs.14744. Epub 2019 Feb 2. PMID: 30600575; PMCID: PMC6850446. 3: Newburg DS, Shea TB, Yatziv S, Raghavan SS, McCluer RH. Macrophages exposed in vitro to conduritol B epoxide resemble Gaucher cells. Exp Mol Pathol. 1988 Jun;48(3):317-23. doi: 10.1016/0014-4800(88)90068-8. PMID: 3371456. 4: Adachi M, Volk BW. Gaucher disease in mice induced by conduritol-B-epoxide: morphologic features. Arch Pathol Lab Med. 1977 May;101(5):255-9. PMID: 576797. 5: Stephens MC, Bernatsky A, Singh H, Kanfer JN, Legler G. Distribution of conduritol B epoxide in the animal model for Gaucher's disease (Gaucher mouse). Biochim Biophys Acta. 1981 Jan 7;672(1):29-32. doi: 10.1016/0304-4165(81)90276-2. PMID: 6783121. 6: Braun H, Legler G, Deshusses J, Semenza G. Stereospecific ring opening of conduritol-B-epoxide by an active site asparatate residue of sucrase-isomaltase. Biochim Biophys Acta. 1977 Jul 8;483(1):135-40. doi: 10.1016/0005-2744(77)90015-8. PMID: 560212. 7: Yang SJ, Ge SG, Zeng YC, Zhang SZ. Inactivation of alpha-glucosidase by the active-site-directed inhibitor, conduritol B epoxide. Biochim Biophys Acta. 1985 Apr 29;828(3):236-40. PMID: 3886011. 8: Grabowski GA, Dinur T, Osiecki KM, Kruse JR, Legler G, Gatt S. Gaucher disease types 1, 2, and 3: differential mutations of the acid beta-glucosidase active site identified with conduritol B epoxide derivatives and sphingosine. Am J Hum Genet. 1985 May;37(3):499-510. PMID: 4003396; PMCID: PMC1684582. 9: Jo J, Yang L, Tran HD, Yu W, Sun AX, Chang YY, Jung BC, Lee SJ, Saw TY, Xiao B, Khoo ATT, Yaw LP, Xie JJ, Lokman H, Ong WY, Lim GGY, Lim KL, Tan EK, Ng HH, Je HS. Lewy Body-like Inclusions in Human Midbrain Organoids Carrying Glucocerebrosidase and α-Synuclein Mutations. Ann Neurol. 2021 Sep;90(3):490-505. doi: 10.1002/ana.26166. Epub 2021 Aug 10. PMID: 34288055; PMCID: PMC9543721. 10: Balreira A, Cavallari M, Sá Miranda MC, Arosa FA. Uncoupling between CD1d upregulation induced by retinoic acid and conduritol-B-epoxide and iNKT cell responsiveness. Immunobiology. 2010 Jun;215(6):505-13. doi: 10.1016/j.imbio.2009.07.002. Epub 2009 Aug 3. PMID: 19651460. 11: Newburg DS, Yatziv S, McCluer RH, Raghavan S. beta-Glucosidase inhibition in murine peritoneal macrophages by conduritol-B-epoxide: an in vitro model of the Gaucher cell. Biochim Biophys Acta. 1986 Jun 11;877(1):121-6. doi: 10.1016/0005-2760(86)90126-8. PMID: 3087427. 12: Stephens MC, Bernatsky A, Burachinsky V, Legler G, Kanfer JN. The Gaucher mouse: differential action of conduritol B epoxide and reversibility of its effects. J Neurochem. 1978 May;30(5):1023-7. doi: 10.1111/j.1471-4159.1978.tb12395.x. PMID: 96213. 13: Serrano P, Llebaria A, Delgado A. Regio- and stereoselective synthesis of aminoinositols and 1,2-diaminoinositols from conduritol B epoxide. J Org Chem. 2005 Sep 30;70(20):7829-40. doi: 10.1021/jo050521a. Erratum in: J Org Chem. 2006 Jan 6;71(1):448. PMID: 16277302. 14: Grabowski GA, Osiecki-Newman K, Dinur T, Fabbro D, Legler G, Gatt S, Desnick RJ. Human acid beta-glucosidase. Use of conduritol B epoxide derivatives to investigate the catalytically active normal and Gaucher disease enzymes. J Biol Chem. 1986 Jun 25;261(18):8263-9. PMID: 3087971. 15: Premkumar L, Sawkar AR, Boldin-Adamsky S, Toker L, Silman I, Kelly JW, Futerman AH, Sussman JL. X-ray structure of human acid-beta-glucosidase covalently bound to conduritol-B-epoxide. Implications for Gaucher disease. J Biol Chem. 2005 Jun 24;280(25):23815-9. doi: 10.1074/jbc.M502799200. Epub 2005 Apr 6. PMID: 15817452. 16: Hayashi Y, Ito M. Klotho-Related Protein KLrP: Structure and Functions. Vitam Horm. 2016;101:1-16. doi: 10.1016/bs.vh.2016.02.011. Epub 2016 Mar 29. PMID: 27125736. 17: Zurbruegg M, Chan MY, Svenningsson P. GBA RNAi but not catalytic inhibition of glucocerebrosidase with Conduritol-β-epoxide increases levels of total α-synuclein in SH-SY5Y cells. Neurosci Lett. 2019 Jul 27;706:217-222. doi: 10.1016/j.neulet.2019.05.027. Epub 2019 May 15. PMID: 31102708. 18: Daniels LB, Glew RH, Radin NS, Vunnam RR. A revised fluorometric assay for Gaucher's disease using conduritol-beta-epoxide with liver as the source of Beta-glucosidase. Clin Chim Acta. 1980 Sep 25;106(2):155-63. doi: 10.1016/0009-8981(80)90168-0. PMID: 6773704. 19: Ishibashi Y, Kohyama-Koganeya A, Hirabayashi Y. New insights on glucosylated lipids: metabolism and functions. Biochim Biophys Acta. 2013 Sep;1831(9):1475-85. doi: 10.1016/j.bbalip.2013.06.001. Epub 2013 Jun 13. PMID: 23770033. 20: Su Q, Schröder SP, Lelieveld LT, Ferraz MJ, Verhoek M, Boot RG, Overkleeft HS, Aerts JMFG, Artola M, Kuo CL. Corrigendum: Xylose-Configured Cyclophellitols as Selective Inhibitors for Glucocerebrosidase. Chembiochem. 2022 Dec 29:e202200728. doi: 10.1002/cbic.202200728. Epub ahead of print. Erratum for: Chembiochem. 2021 Nov 3;22(21):3090-3098. PMID: 36581583.