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MedKoo Cat#: 584503 | Name: Allolactose
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Description:

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

Allolactose is a disaccharide similar to lactose. It is an inducer of the lac operon in Escherichia coli and many other enteric bacteria.

Chemical Structure

Allolactose
CAS#28447-39-4

Theoretical Analysis

MedKoo Cat#: 584503

Name: Allolactose

CAS#: 28447-39-4

Chemical Formula: C12H22O11

Exact Mass: 342.1162

Molecular Weight: 342.30

Elemental Analysis: C, 42.11; H, 6.48; O, 51.41

Price and Availability

Size Price Availability Quantity
100mg USD 750.00 2 Weeks
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Synonym
Allolactose
IUPAC/Chemical Name
6-O-beta-D-Galactopyranosyl-D-glucopyranose
InChi Key
DLRVVLDZNNYCBX-VDGMBKLFSA-N
InChi Code
InChI=1S/C12H22O11/c13-1-3-5(14)8(17)10(19)12(23-3)21-2-4-6(15)7(16)9(18)11(20)22-4/h3-20H,1-2H2/t3-,4-,5+,6-,7+,8+,9-,10-,11?,12-/m1/s1
SMILES Code
OC1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@H]([C@@H](CO)O2)O)O)O)O1)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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 342.30 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: Juers DH, Matthews BW, Huber RE. LacZ β-galactosidase: structure and function of an enzyme of historical and molecular biological importance. Protein Sci. 2012 Dec;21(12):1792-807. doi: 10.1002/pro.2165. Epub 2012 Nov 13. PMID: 23011886; PMCID: PMC3575911. 2: Wheatley RW, Huber RE. An allolactose trapped at the lacZ β-galactosidase active site with its galactosyl moiety in a (4)H3 conformation provides insights into the formation, conformation, and stabilization of the transition state. Biochem Cell Biol. 2015 Dec;93(6):531-40. doi: 10.1139/bcb-2015-0037. Epub 2015 Jun 25. PMID: 26291713. 3: Huber RE, Wallenfels K, Kurz G. The action of beta-galactosidase (Escherichia coli) on allolactose. Can J Biochem. 1975 Sep;53(9):1035-8. doi: 10.1139/o75-142. PMID: 241475. 4: Aggarwal RK, Narang A. Positive feedback exists and drives the glucose- mediated repression in Escherichia coli. Biophys J. 2022 Mar 1;121(5):808-819. doi: 10.1016/j.bpj.2022.01.017. Epub 2022 Jan 20. PMID: 35065914; PMCID: PMC8943705. 5: Hall BG. Transgalactosylation activity of ebg beta-galactosidase synthesizes allolactose from lactose. J Bacteriol. 1982 Apr;150(1):132-40. doi: 10.1128/jb.150.1.132-140.1982. PMID: 6801019; PMCID: PMC220091. 6: Wheatley RW, Lo S, Jancewicz LJ, Dugdale ML, Huber RE. Structural explanation for allolactose (lac operon inducer) synthesis by lacZ β-galactosidase and the evolutionary relationship between allolactose synthesis and the lac repressor. J Biol Chem. 2013 May 3;288(18):12993-3005. doi: 10.1074/jbc.M113.455436. Epub 2013 Mar 13. PMID: 23486479; PMCID: PMC3642343. 7: Turner CL, Huber RE. Differential binding of allolactose anomers to the lactose repressor of Escherichia coli. J Mol Biol. 1977 Sep 15;115(2):195-9. doi: 10.1016/0022-2836(77)90096-1. PMID: 338908. 8: Huber RE, Hakda S, Cheng C, Cupples CG, Edwards RA. Trp-999 of beta- galactosidase (Escherichia coli) is a key residue for binding, catalysis, and synthesis of allolactose, the natural lac operon inducer. Biochemistry. 2003 Feb 18;42(6):1796-803. doi: 10.1021/bi0270642. PMID: 12578395. 9: Huber RE, Kurz G, Wallenfels K. A quantitation of the factors which affect the hydrolase and transgalactosylase activities of beta-galactosidase (E. coli) on lactose. Biochemistry. 1976 May 4;15(9):1994-2001. doi: 10.1021/bi00654a029. PMID: 5122. 10: Huber RE, Hurlburt KL. Reversion reactions of beta-galactosidase (Escherichia coli). Arch Biochem Biophys. 1986 Apr;246(1):411-8. doi: 10.1016/0003-9861(86)90487-x. PMID: 3083779. 11: Wong P, Gladney S, Keasling JD. Mathematical model of the lac operon: inducer exclusion, catabolite repression, and diauxic growth on glucose and lactose. Biotechnol Prog. 1997 Mar-Apr;13(2):132-43. doi: 10.1021/bp970003o. PMID: 9104037. 12: LESPAGNOL A, MONTREUIL J, SEGARD E. [The problem of "allolactose" of human milk]. C R Seances Soc Biol Fil. 1960;154:130-2. French. PMID: 14416018. 13: Hodgson R, Mahid T, Nelson A. Directed and undirected asymmetric dihydroxylation reactions: application in the synthesis of a C-linked analogue of allolactose. Chem Commun (Camb). 2001 Oct 21;(20):2076-7. doi: 10.1039/b107643d. PMID: 12240170. 14: Myung SH, Park J, Han JH, Kim TH. Development of the Mammalian Expression Vector System that can be Induced by IPTG and/or Lactose. J Microbiol Biotechnol. 2020 Aug 28;30(8):1124-1131. doi: 10.4014/jmb.2003.03030. PMID: 32423185; PMCID: PMC9728253. 15: Hartz P, Mattes C, Schad M, Bernhardt R, Hannemann F. Expanding the promoter toolbox of Bacillus megaterium. J Biotechnol. 2019 Mar 20;294:38-48. doi: 10.1016/j.jbiotec.2019.01.018. Epub 2019 Feb 13. PMID: 30771444. 16: Ambrogi V, Bottacini F, Mac Sharry J, van Breen J, O'Keeffe E, Walsh D, Schoemaker B, Cao L, Kuipers B, Lindner C, Jimeno ML, Doyagüez EG, Hernandez- Hernandez O, Moreno FJ, Schoterman M, van Sinderen D. Bifidobacterial β-Galactosidase-Mediated Production of Galacto-Oligosaccharides: Structural and Preliminary Functional Assessments. Front Microbiol. 2021 Oct 28;12:750635. doi: 10.3389/fmicb.2021.750635. PMID: 34777303; PMCID: PMC8581567. 17: Yildirim N, Santillan M, Horike D, Mackey MC. Dynamics and bistability in a reduced model of the lac operon. Chaos. 2004 Jun;14(2):279-92. doi: 10.1063/1.1689451. PMID: 15189056. 18: Julio-Gonzalez LC, Moreno FJ, Jimeno ML, Doyagüez EG, Olano A, Corzo N, Hernandez-Hernandez O. Hydrolysis and transglycosylation activities of glycosidases from small intestine brush-border membrane vesicles. Food Res Int. 2021 Jan;139:109940. doi: 10.1016/j.foodres.2020.109940. Epub 2020 Dec 3. PMID: 33509494. 19: Spiwok V, Lipovová P, Skálová T, Buchtelová E, Hasek J, Králová B. Role of CH/pi interactions in substrate binding by Escherichia coli beta-galactosidase. Carbohydr Res. 2004 Sep 13;339(13):2275-80. doi: 10.1016/j.carres.2004.06.016. PMID: 15337456. 20: Yildirim N, Mackey MC. Feedback regulation in the lactose operon: a mathematical modeling study and comparison with experimental data. Biophys J. 2003 May;84(5):2841-51. doi: 10.1016/S0006-3495(03)70013-7. Erratum in: Biophys J. 2007 Jan 15;92(2):699. PMID: 12719218; PMCID: PMC1302849.