Lactobionic acid

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Lactobionic acid
Category Others
Catalog number BBF-03757
CAS 96-82-2
Molecular Weight 358.29
Molecular Formula C12H22O12

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Description

A disaccharide sugar acid derived from galactose and gluconate.

Specification

Synonyms 4-O-b-D-Galactopyranosyl-D-gluconic acid; 4-(beta-D-Galactosido)-D-gluconic acid
Storage Tightly closed. Dry.
IUPAC Name (2R,3R,4R,5R)-2,3,5,6-tetrahydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanoic acid
Canonical SMILES C(C1C(C(C(C(O1)OC(C(CO)O)C(C(C(=O)O)O)O)O)O)O)O
InChI InChI=1S/C12H22O12/c13-1-3(15)10(7(18)8(19)11(21)22)24-12-9(20)6(17)5(16)4(2-14)23-12/h3-10,12-20H,1-2H2,(H,21,22)/t3-,4-,5+,6+,7-,8-,9-,10-,12+/m1/s1
InChI Key JYTUSYBCFIZPBE-AMTLMPIISA-N

Properties

Appearance White Powder
Boiling Point 864.7°C at 760 mmHg
Melting Point 113-118°C(lit.)
Density 1.79 g/cm3
Solubility Soluble in Water (10 g/100 mL)

Reference Reading

1.Simultaneous production of lactobionic and gluconic acid in cheese whey/glucose co-fermentation by Pseudomonas taetrolens.
Alonso S1, Rendueles M1, Díaz M2. Bioresour Technol. 2015 Nov;196:314-23. doi: 10.1016/j.biortech.2015.07.092. Epub 2015 Jul 29.
Substrate versatility of Pseudomonas taetrolens was evaluated for the first time in a co-fermentation system combining cheese whey and glucose, glycerol or lactose as co-substrates. Results showed that P. taetrolens displayed different production patterns depending on the co-substrate supplied. Whereas the presence of glucose led to a simultaneous co-production of lactobionic (78g/L) and gluconic acid (8.8g/L), lactose feeding stimulated the overproduction of lactobionic acid from whey with a high specific productivity (1.4g/gh) and yield (100%). Co-substrate supply of glycerol conversely led to reduced lactobionic acid yield (82%) but higher cell densities (1.8g/L), channelling the carbon source towards cell growth and maintenance. Higher carbon availability impaired the metabolic activity as well as membrane integrity, whereas lactose feeding improved the cellular functionality of P. taetrolens. Insights into these mixed carbon source strategies open up the possibility of co-producing lactobionic and gluconic acid into an integrated single-cell biorefinery.
2.Effect of lactobionic acid on the acidification, rheological properties and aroma release of dairy gels.
Ribeiro JC1, Granato D2, Masson ML3, Andriot I4, Mosca AC5, Salles C6, Guichard E7. Food Chem. 2016 Sep 15;207:101-6. doi: 10.1016/j.foodchem.2016.03.066. Epub 2016 Mar 19.
The food industry is investigating new technological applications of lactobionic acid (LBA). In the current work, the effect of lactobionic acid on the acidification of dairy gels (pH 5.5 and 6.2), rheological properties using a double compression test, sodium mobility using (23)Na NMR technique and aroma release using headspace GC-FID were studied. Our results showed that it is possible to use LBA as an alternative to glucono-δ-lactone (GDL) for the production of dairy gels with a controlled pH value. Small differences in the rheological properties and in the amount of aroma volatile organic compounds that were released in the vapour phase, but no significant difference in the sodium ion mobility were obtained. The gels produced with LBA were less firm and released less volatile aroma compounds than the gels produced with GDL. The gels at pH 6.2 were firmer than those at pH 5.5 and had a more organised structure around the sodium ions.
3.Targeted delivery of doxorubicin by lactobionic acid-modified laponite to hepatocarcinoma cells.
Chen G1, Li D2, Li J1, Luo Y1, Wang J3, Shi X4, Guo R5. J Control Release. 2015 Sep 10;213:e34. doi: 10.1016/j.jconrel.2015.05.054. Epub 2015 Aug 19.
4.Tailored Synthesis of Octopus-type Janus Nanoparticles for Synergistic Actively-Targeted and Chemo-Photothermal Therapy.
Zhang L1, Chen Y2, Li Z3, Li L4, Saint-Cricq P3, Li C5, Lin J2, Wang C6, Su Z1, Zink JI3. Angew Chem Int Ed Engl. 2016 Feb;55(6):2118-21. doi: 10.1002/anie.201510409. Epub 2016 Jan 6.
A facile, reproducible, and scalable method was explored to construct uniform Au@poly(acrylic acid) (PAA) Janus nanoparticles (JNPs). The as-prepared JNPs were used as templates to preferentially grow a mesoporous silica (mSiO2 ) shell and Au branches separately modified with methoxy-poly(ethylene glycol)-thiol (PEG) to improve their stability, and lactobionic acid (LA) for tumor-specific targeting. The obtained octopus-type PEG-Au-PAA/mSiO2 -LA Janus NPs (PEG-OJNP-LA) possess pH and NIR dual-responsive release properties. Moreover, DOX-loaded PEG-OJNP-LA, upon 808 nm NIR light irradiation, exhibit obviously higher toxicity at the cellular and animal levels compared with chemotherapy or photothermal therapy alone, indicating the PEG-OJNP-LA could be utilized as a multifunctional nanoplatform for in vitro and in vivo actively-targeted and chemo-photothermal cancer therapy.

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