Disease relevance of trehalose

• The effects that polycation structure has on toxicity and gene delivery efficiency are investigated here by synthesizing a series of amidine-based polycations that contain the carbohydrates d-trehalose and beta-cyclodextrin (CD) within the polycation backbone [1].
• A previous paper indicated that corynomycolates synthesized by the fluffy layer fraction prepared from Corynebacterium matruchotii cells appeared exclusively as alpha-trehalose 6-monocorynomycolate (TMM) (T. Shimakata, K. Tsubokura, T. Kusaka, and K. Shizukuishi, 1985, Arch. Biochem. Biophys. 238, 497-508) [2].
• The isolates could be differentiated from other Prevotella species by D-mannitol, D-melezitose, D-sorbitol and D-trehalose fermentation in API 20A tests [3].
• With a view to gaining evidence on the mechanism by which D-trehalose is able to stabilise biomolecules towards dehydration (anhydrobiosis) and heat, L-trehalose has been prepared in order to allow comparative studies to be made [4].
• In this paper we examine the use of alpha, alpha-trehalose-borate systems as protectants for Lactobacillus acidophilus during freeze- and vacuum-drying [5].

High impact information on trehalose

• The Bacillus sp. SAM1606 alpha-glucosidase with a broad substrate specificity is the only known alpha-glucosidase that can hydrolyze alpha,alpha'-trehalose efficiently [6].
• While the physiological function of Ag85, a mycolyltransferase required for the biosynthesis of the cell wall component alpha,alpha'-trehalose dimycolate (or cord factor), has been identified recently, the function of the closely related MPT51 (approximately 40% identity with the Ag85 components) remains to be established [7].
• Moreover, the absence of a recognizable alpha,alpha'-trehalose monomycolate-binding site and the failure to detect an active site suggest that the function of MPT51 is of a non-enzymatic nature and that MPT51 may in fact represent a new family of non-catalytic alpha/beta hydrolases [7].
• A series of quaternary ammonium polycations containing N,N,N',N'-tetramethyl-1,6-hexanediamine, d-trehalose, and beta-cyclodextrin are synthesized in order to elucidate the effects of charge center type (by comparison to the data given in Part 1) on gene delivery [8].
• The alpha-glucosidase of Bacillus sp. strain SAM1606 is a member of glycosyl hydrolase family 13, and shows an extraordinarily broad substrate specificity and is one of very few alpha-glucosidases that can efficiently hydrolyze the alpha-1,1-glucosidic linkage of alpha,alpha'-trehalose (trehalose) [9].

Chemical compound and disease context of trehalose

• Comparison of the ability of the enantiomeric forms of trehalose to stabilise alkaline phosphatase towards dehydration and heat showed that natural D-trehalose is superior to L-trehalose, although both disaccharides provide some protection for the enzyme [10].
• The gene encoding trehalose synthase (catalyzing the conversion of maltose into alpha, alpha-trehalose by transglucosylation) was cloned from Thermus aquaticus ATCC33923 [11].

Biological context of trehalose

• Reaction of 2,3,4,2',3',4'-hexa-O-acetyl- 6,6'-di-O-tosyl-alpha, alpha-trehalose with sodium dicarbonylcyclopentadienyliron, followed by oxidative hydrolysis or methanolysis, gave the 2,3,4,2',3',4'-hexa-acetate of 7 or its dimethyl ester, respectively [12].
• This compound was used directly in a trimethylsilyl triflate-mediated glycosylation reaction with 2,3,6-tri-O-benzyl-alpha-D-glucopyranosyl 2,3-di-O-benzyl-4,6-O-benzylidene-alpha-D-glucopyranoside to give the corresponding maltosyl-(1-->4)-alpha, alpha-trehalose derivative [13].
• The labelling of alpha,alpha'-trehalose indicated that gluconeogenesis and the hexose monophosphate pathway operate in a similar way to the wild-type [14].

Anatomical context of trehalose

• Optimum development of in vitro culture of frozen-thawed biopsied blastocysts was obtained using 1.8 M EG + 0.05 M T and 20% PVP [15].
• Trehalase (alpha, alpha-trehalose glucohydrolase, EC 3.2.1.28) was solubilized from the brush-border membrane of rabbit intestine and kidney by Emulphogen BC 720 [16].
• Injection of adult male cockroaches (Periplaneta americana) with 10 microliter 1 microM octopamine causes elevated activity of trehalase (alpha, alpha-trehalose glucohydrolase; EC 3.2.1.28) in hemolymph and muscle but not in gut [17].

Associations of trehalose with other chemical compounds

• D-trehalose/D-maltose-binding protein from the hyperthermophilic archaeon Thermococcus litoralis: the binding of trehalose and maltose results in different protein conformational states [18].
• Carbodiimide modification of the Rhynchosciara americana midgut trehalase (alpha, alpha-trehalose glucohydrolase, EC 3.2.1.28) at different pH values revealed the existence of two essential groups (pKa 5.28 and pKa 7.74) for the trehalos activity [19].

Gene context of trehalose

• Alternatively, cyanide displacement of hexa-O-acetyl-alpha, alpha-trehalose 6,6'-ditriflate gave the dinitrile hexa-acetate of 7, which was O-deacetylated and then hydrolyzed with alkaline hydrogen peroxide to yield 7 [12].
• Trehalose-induced autophagy enhanced the clearance of autophagy substrates like mutant huntingtin and the A30P and A53T mutants of alpha-synuclein, associated with Huntington disease (HD) and Parkinson disease (PD), respectively [20].

Analytical, diagnostic and therapeutic context of trehalose

• The proportion of biopsied blastocysts that reexpanded following cryopreservation in 1.8 M EG + 0.05 M T (38.5%) and 1.8 M EG + 0.1 M T (36.1%) was significantly (P < 0.05) higher than the proportion that reexpanded in 1.8 M EG + 0.3 M T (13.9%) (Experiment 2) [15].

References