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PubMed1991

A nuclear magnetic resonance spectroscopic and conformational study of eight pseudo-trehaloses (D-glucopyranosyl 5a-carba-D- and -L-glucopyranosides).

N.m.r. data (1H and 13C) are presented for eight pseudo-trehalose derivatives in which the D-glucopyranosyl moiety is alpha or beta and the 5a-carbaglucopyranoside moiety is alpha-D, beta-D, alpha-L, or beta-L. The differences in the chemical shifts and then n.O.e. effects have been correlated with the preferred conformations estimated from empirical force-field calculations (HSEA), which have been used to calculate the average parameters over the whole energy surface. Of the four alpha-D-glucopyranosyl derivatives, only that with a 5a-carba-beta-D-glucopyranoside moiety (3) was a substrate for glucoamylase.

Carbohydrate Conformation↗
PubMed1993

An improved synthesis of 4-azido-4-deoxy- and 4-amino-4-deoxy-alpha,alpha-trehalose and their epimers.

The order of esterification of the eight hydroxyl groups of alpha,alpha-trehalose is HO-6.6' > HO-2.2' > HO-3.3' > HO-4.4'. Under the appropriate conditions of benzoylation, the heptabenzoate with HO-4' free was obtained in good yield (58%), along with the octabenzoate and the hexabenzoate having HO-4.4' free. The readily isolated heptabenzoate was a convenient starting material for the synthesis of 4-azido-4-deoxy- (84%) and 4-amino-4-deoxy-alpha-D-galactopyranosyl alpha-D-glucopyranoside, and the heptabenzoate of alpha-D-galactopyranosyl alpha-D-glucopyranoside with HO-4' free, which was used as a synthetic precursor of 4-azido-4-deoxy-alpha-D-glucopyranosyl alpha-D-glucopyranoside and its amino analogue.

Azides↗
PubMed1989

Simulation of the activation of fat body glycogen phosphorylase and trehalose synthesis by peptide hormones in the American cockroach.

A model is described which simulates activation of glycogen phosphorylase and induction of trehalose synthesis in the fat body of the American cockroach, Periplaneta americana, by two hypertrehalosaemic peptides. Parameters for the model were estimated from literature data (Siegert et al., Insect Biochem. 16, 365), with the exception of the half-life of the physiologically active peptides, which was estimated from the model. The model describes satisfactorily the activation of glycogen phosphorylase and the increase of haemolymph carbohydrates, which is dependent on the activation of glycogen phosphorylase in the model. It further explains the observed differences in sensitivity for glycogen phosphorylase activation and increase in haemolymph carbohydrates by these peptides. Best fits were obtained with a physiological half-life of about 12-15 min for the peptides. This value is similar to what can be calculated from the in vivo effects of these peptides on heart beat (Gersch et al., Zool. Jb. Physiol. 86, 17), but it is considerably shorter than the published half-life of 1 h for radioactive peptide (Skinner et al., Insect Biochem. 17, 433). However, both values are compatible if part of the peptides in the haemolymph is not present in freely dissolved form, but bound to a haemolymph component. The model half-life would then represent the half-life of the free, physiologically active peptide, which was estimated from the disappearance of radioactive peptide to be about 12-15 min. This suggests, that the model half-life is realistic and physiologically more important than the half-life of radioactive peptide of 1 h.

Animals↗
PubMed1996

Cloning and sequencing of trehalose biosynthesis genes from Arthrobacter sp. Q36.

A 5.1-kbp genomic DNA fragment was cloned from trehalose-producing bacterium Arthrobacter sp. strain Q36. Sequence analysis of the DNA fragment revealed two open reading frames of 2325 and 1794 bp, encoding maltooligosyltrehalose synthase (TreY) and maltooligosyltrehalose trehalohydrolase (TreZ), respectively. The 3' end of treY overlaps with the 5' end of treZ by one nucleotide, and it is suggested that treYZ constitutes and operon. The deduced amino acid sequences of both enzymes have several regions common to amylolytic enzymes belonging to an 'alpha-amylase family'.

Amino Acid Sequence↗
PubMed1996

Regulation of UDPG-pyrophosphorylase isoforms in Saccharomyces cerevisiae and their roles in trehalose metabolism.

UDPG-pyrophosphorylase (EC 2.7.7.9) from Saccharomyces cerevisiae was studied and the presence of isoforms investigated. Its activity was monitored during growth of cultures in rich media containing glucose, galactose, sucrose, maltose or glycerol as carbon sources. The results suggest that UDPG-pyrophosphorylase is subject to both catabolite repression and catabolite inactivation. The inactivation process seems to be complex: in order to produce maximum inactivation, glucose and ammonium sulfate must be added together. Addition of glucose or ammonium sulfate separately produced little effect upon enzyme activity. Adsorption to and elution from a DEAE-Sephacel column of a crude protein extract prepared from yeast cells collected in stationary phase from a glucose medium showed three activity peaks, which we denominated isoform I, II, and III. Isoform I is constitutive, it was the only form present during exponential growth on glucose medium, and did not suffer any alteration after glucose exhaustion, heat shock or by growing cells on maltose. On the other hand, isoforms II and III were shown to be repressed by glucose, and induced by heat shock. Furthermore, isoform II of UDPG-pyrophosphorylase was present together with isoform I when yeast cells were grown on maltose. The presence of a MAL4C allele rendered isoform II constitutive. Interestingly, a gal3 mutant strain had low UDPG-pyrophosphorylase activity and isoforms I and II were not expressed. These results are discussed in relation to trehalose metabolism.

Hot Temperature↗
PubMed1991

Natural abundance 13C-nuclear magnetic resonance spectroscopic analysis of acyclic polyol and trehalose accumulation by several yeast species in response to salt stress.

Analysis of seventeen yeast strains by 13C-NMR spectroscopy has confirmed the significance of glycerol as the sole osmoregulatory solute under salt-stressed conditions, and has shown arabitol to be present in most of the osmotolerant species. Ribitol was detected in some species, including Debaryomyces hansenii, although ribitol accumulation did not correlate with the osmotic pressure of the medium. Relative amounts of arabitol and ribitol decreased in relation to glycerol when the external osmotic pressure was increased. Trehalose was present during exponential growth of some species.

Glycerol↗
PubMed1992

Structure of mycoside F, a family of trehalose-containing glycolipids of Mycobacterium fortuitum.

Nuclear magnetic resonance spectroscopy, fast-atom bombardment mass spectrometry, gas chromatography-mass spectrometry, as well as chemical degradations were used to elucidate the structure of the major glycolipids of Mycobacterium fortuitum. Three main glycoconjugates were detected and their structures established as 2,3-diacyl, 2,3,4- and 2,3,6-triacyl trehalose. The characteristic infrared spectrum which led to their original designation as mycoside F, a family of glycolipids limited in distribution to M. fortuitum, was due to the nature of the fatty acyl substiuents identified primarily as 2-methyl-octadecen-2-oyl. The antigenic glycolipids typified the biovar. fortuitum, thus allowing its easy recognition from the C-mycoside glycopeptidolipid-containing biovar. peregrinum.

Fatty Acids↗
PubMedDate not supplied

Evaluation of a novel 2,3-diacyl-trehalose-2'-sulphate (SL-IV) antigen for case finding and diagnosis of leprosy and tuberculosis.

Serum IgG and IgM antibodies against a 2,3-diacyl-trehalose-2'-sulphate (SL-IV) antigen using ELISA were determined in controls (n = 288) and in leprosy (n = 210) and tuberculosis (n = 99) patients. In all assays, the amount of antigen per well was 100.0 ng and sera were diluted 1/250. In the case of leprosy, anti-SL-IV IgG and IgM antibody titres increased from the tuberculoid towards the lepromatous pole of the spectrum. In the tested population, the sensitivity of the assay was 93.2% in multibacillary leprosy and 33.3% in paucibacillary leprosy (specificity of 88.7%). Multibacillary patients with erythema nodosum leprosum (ENL) had lower titres than non-ENL. ELISA results were similar to those obtained using the Mycobacterium leprae phenolic glycolipid-I (PGL-I) antigen. In the case of tuberculosis (pulmonary and extrapulmonary), significant titres of anti SL-IV IgG and IgM antibodies were detected in about 75% of the patients using a cutoff point of 0.150, and in 51.6% using a cutoff of 0.300 (specificities were, respectively, 88% and 100%). We concluded that the determination of IgG and IgM antibodies against SL-IV was useful in leprosy and tuberculosis case finding program using a cutoff point of 0.150, and for serodiagnosis using a cutoff of 0.300.

Antigens, Bacterial↗
PubMed2005

Internal dynamics and protein-matrix coupling in trehalose-coated proteins.

We review recent studies on the role played by non-liquid, water-containing matrices on the dynamics and structure of embedded proteins. Two proteins were studied, in water-trehalose matrices: a water-soluble protein (carboxy derivative of horse heart myoglobin) and a membrane protein (reaction centre from Rhodobacter sphaeroides). Several experimental techniques were used: Mossbauer spectroscopy, elastic neutron scattering, FTIR spectroscopy, CO recombination after flash photolysis in carboxy-myoglobin, kinetic optical absorption spectroscopy following pulsed and continuous photoexcitation in Q(B) containing or Q(B) deprived reaction centre from R. sphaeroides. Experimental results, together with the outcome of molecular dynamics simulations, concurred to give a picture of how water-containing matrices control the internal dynamics of the embedded proteins. This occurs, in particular, via the formation of hydrogen bond networks that anchor the protein surface to the surrounding matrix, whose stiffness increases by lowering the sample water content. In the conclusion section, we also briefly speculate on how the protein-matrix interactions observed in our samples may shed light on the protein-solvent coupling also in liquid aqueous solutions.

Computer Simulation↗
PubMed2005

Correlation between bioprotective effectiveness and dynamic properties of trehalose-water, maltose-water and sucrose-water mixtures.

The aim of the present work is to link the bioprotective effectiveness to the dynamic properties of a class of homologous disaccharides, that is, trehalose, maltose and sucrose, and their mixtures in water. The findings obtained by elastic neutron scattering point out a harmonic-anharmonic transition for all the three disaccharide mixtures. Using a new operative definition of 'fragility', the different degrees of 'strength' of the investigated systems are determined. The links existing between the degree of fragility and the cryptoprotective action are also discussed.

Maltose↗
PubMed2005

A small stress protein acts synergistically with trehalose to confer desiccation tolerance on mammalian cells.

The ability to desiccate mammalian cells while maintaining a high degree of viability would be very important in many areas of biological science, including tissue engineering, cell transplantation, and biosensor technologies. Certain proteins and sugars found in animals capable of surviving desiccation might aid this process. We report here that human embryonic kidney (293H) cells transfected with the gene for the stress protein p26 from Artemia and loaded with trehalose showed a sharp increase in survival during air-drying. Further, we find vacuum-drying greatly improved the ability of the cells to survive, and that the physical shape and structure of the cellular sample had a large influence on recovery following rehydration. Cells suspended in a rounded droplet survived desiccation markedly better than those spread as a thin film. Finally, we used alamarBlue to monitor cellular metabolism and Hema 3 to assess colony formation after vacuum-drying. AlamarBlue fluorescence indicated that the transfected 293H cells expressing p26 (E11'L) grew much better than the control 293H cells. In fact, immediate survival and colony formation in E11'L cells increased as much as 34-fold compared with control cells when the samples were dried to a water content of 0.2 g H2O/g dry weight, as measured by gravimetric analysis. These results indicate that p26 improves cell survival following drying and rehydration, and suggest that dry storage of mammalian cells is a likely possibility in the future.

Air↗
PubMed2005

Osmotically induced trehalose and glycine betaine accumulation improves tolerance to desiccation, survival and efficacy of the postharvest biocontrol agent Pantoea agglomerans EPS125.

The application of the biocontrol agent Pantoea agglomerans EPS125 to unwounded fruits was practically ineffective for control of postharvest blue mould caused by Penicillium expansum when the treatment and subsequent wounding and pathogen inoculation were separated by periods of unfavourable conditions. This was due to a rapid decrease in viability of the alocthonous introduced biocontrol agent in the intact peel surface. A system for osmoadaptation of the biocontrol agent was developed by combining saline osmotic stress and osmolyte amendment to the growth medium. Osmoadapted cells accumulated trehalose and glycine betaine (GB) intracellularly and showed a higher tolerance to desiccation than non-osmoadapted cells. Osmoadaptation in NaCl plus GB during inoculum preparation increased considerably survival on the peel surface of apple fruits. This effect was significant under low relative humidity (RH) and fluctuating RH conditions, but was not significant at high RH. Osmoadaptation significantly improved blue mould control under conditions where the standard biological control treatments were ineffective. The rot diameter was significantly reduced in apple fruits which were treated with EPS125 and incubated for several days under low, high or fluctuating RH, followed by wounding and inoculation of P. expansum. Growth of EPS125 with NaCl, either with or without the addition of GB, was an effective osmoadaptation treatment for improving blue mould rot control. However, the addition of GB to the NaCl amended growth medium increased 4-5-fold growth rate and OD of the cultures. This is an advantage for mass production of P. agglomerans EPS125 in a NaCl amended growth medium.

Adaptation, Physiological↗
PubMed2006

Freeze-dried whole plasma: evaluating sucrose, trehalose, sorbitol, mannitol and glycine as stabilizers.

Several groups report stability results for freeze-dried whole plasma intended for use as a transfusion product [Hellstern P, Sachse H, Schwinn H, Oberfrank K. Manufacture and in vitro characterization of a solvent/detergent-treated human plasma. Vox Sang 1992;63:178-185; Trobisch H. Results of a quality-control study of lyophilized pooled plasmas which have been virally inactivated using a solvent detergent method (modified Horowitz procedure). Beitr Infusionsther 1991;28:92-109; Hugler P, Trobish H, Neuman H, Moller, Sirtl C, Derdak M, Laubenthal H. Quality control of three different conventional fresh-frozen plasma preparations and one new virus-inactivated lyophilized pooled plasma preparation. Klin Wochenschr 1991;69:157-161; Krutvacho T, Chuansumrit A, Isarangkura P, Pintadit P, Hathirat P, Chiewsilp P. Response of hemophilia with bleeding to fresh dry plasma. Southeast Asian J Trop Med Public Health 1993;24:169-173; Chuansumrit A, Krasaesub S, Angchaisuksiri P, Hathirat P, Isarangkura P. Survival analysis of patients with haemophilia at the International Haemophilia Training Centre, Bangkok, Thailand. Haemophilia 2004;10:542-549]. Plasma coagulation properties are substantially impaired in these freeze-dried plasmas, while pH levels are close to alkaline. In this work, plasma supplemented with 60mM sucrose, trehalose, mannitol, sorbitol or glycine was freeze-dried. The samples were subjected to forced degradation at 40 degrees C for 10 days in order to quickly evaluate the effectiveness of the different stabilizers. Initial PT, APTT and TT values were 14.4+/-0. 5s, 31.4+/-1.5s and 18.3+/-0.6s, respectively. At the end of the degradation period, PT, APTT and TT were substantially prolonged, and were 19.1+/-0. 5s, 43.1+/-0.6s and 26.1+/-1.0s, respectively. In the presence of glycine, at the end of the degradation period, PT, APTT and TT values remained close to the initial values and were 15.5+/-0. 4s, 35.7+/-0.9s and 19.4+/-0.2s, respectively. Percent activities of the coagulation factors V, VII, VIII, IX, X and the coagulation inhibitors protein C, protein S and antithrombin III were recorded. Factors V and VIII were most prone to degradation. Factor V and VIII activities, in control plasma, were approx. 44+/-3.5% and 58+/-2.3%, at the end of storage. In contrast, much higher factor V and VIII activities were maintained in the lyophilized glycine-supplemented plasma: approx. 60+/-3.5% and 74+/-7.0%, correspondingly. The most stable protein was protein C, which showed no signs of degradation under the testing conditions of this study. All tested stabilizers provided protection. Glycine, however, outperformed all tested polyols, providing superior preservation of plasma clotting properties. Thermograms of 60mM glycine in water and 60mM glycine in plasma show that, in the presence of plasma, glycine does not crystallize. The process of freeze-drying caused a complete loss of plasma pCO(2) (gas) and a substantial increase in plasma pH. Citric acid was found to be a suitable pH adjuster for lyophilized/rehydrated plasma.

Blood Preservation↗
PubMed2003

Residual water modulates QA- -to-QB electron transfer in bacterial reaction centers embedded in trehalose amorphous matrices.

The role of protein dynamics in the electron transfer from the reduced primary quinone, Q(A)(-), to the secondary quinone, Q(B), was studied at room temperature in isolated reaction centers (RC) from the photosynthetic bacterium Rhodobacter sphaeroides by incorporating the protein in trehalose water systems of different trehalose/water ratios. The effects of dehydration on the reaction kinetics were examined by analyzing charge recombination after different regimes of RC photoexcitation (single laser pulse, double flash, and continuous light) as well as by monitoring flash-induced electrochromic effects in the near infrared spectral region. Independent approaches show that dehydration of RC-containing matrices causes reversible, inhomogeneous inhibition of Q(A)(-)-to-Q(B) electron transfer, involving two subpopulations of RCs. In one of these populations (i.e., active), the electron transfer to Q(B) is slowed but still successfully competing with P(+)Q(A)(-) recombination, even in the driest samples; in the other (i.e., inactive), electron transfer to Q(B) after a laser pulse is hindered, inasmuch as only recombination of the P(+)Q(A)(-) state is observed. Small residual water variations ( approximately 7 wt %) modulate fully the relative fraction of the two populations, with the active one decreasing to zero in the driest samples. Analysis of charge recombination after continuous illumination indicates that, in the inactive subpopulation, the conformational changes that rate-limit electron transfer can be slowed by >4 orders of magnitude. The reported effects are consistent with conformational gating of the reaction and demonstrate that the conformational dynamics controlling electron transfer to Q(B) is strongly enslaved to the structure and dynamics of the surrounding medium. Comparing the effects of dehydration on P(+)Q(A)(-)-->PQ(A) recombination and Q(A)(-)Q(B)-->Q(A)Q(B)(-) electron transfer suggests that conformational changes gating the latter process are distinct from those stabilizing the primary charge-separated state.

Desiccation↗
PubMed2002

Supercritical CO(2) fluid extraction of crystal water from trehalose dihydrate. Efficient production of form II (T(alpha)) phase.

Form II is a kind of metastable crystalline form of trehalose anhydrate, and it is easily converted to the dihydrate crystal by absorbing water in moist atmosphere at room temperature (Akao et al., Carbohydr. Res. 2001, 334, 233-241). It can be utilized as an edible and nontoxic desiccant, and thus its efficient production from the dihydrate is significant from a viewpoint of industrial applications. In this study, we attempt to extract crystal water from the dihydrate using supercritical CO(2). We examine the dependence of extraction efficiency on the extraction time, the temperature and pressure of the fluid. Then, FTIR measurements are carried out to detect the extracted water and to identify the polymorphic phase of the sugar sample after the extraction treatment. In particular, the so-called first derivative euclidean distance analysis for IR spectra is shown to be quite useful for the structural identification. Consequently, we demonstrate that form II is produced from the dihydrate through supercritical CO(2) fluid extraction if appropriate temperature and pressure conditions (around 80 degrees C and 20 MPa) are maintained.

Carbon Dioxide↗
PubMed2003

Activity coefficients of NaCl in trehalose-water and maltose-water mixtures at 298.15 K.

The ionic mean activity coefficients of NaCl in trehalose-water and maltose-water mixtures have been experimentally determined at 298.15 K from emf measurements by electrochemical cell containing ion selective electrodes (ISE): Na-ISE/NaCl (m), sugar (Y%), H(2)O (100-Y%)/Cl-ISE. The electrolyte molality (m) ranged between 0.01 and 3 mol kg(-1), approximately, and the weight percent (Y%) of sugar in the mixture of solvents between 0, 10, 20, 30 and 40%. The system is considered as an electrolyte in a mixture of solvents and the data have been analysed by using the Debye-Hückel and Pitzer equations. The results obtained with both equations are in quite agreement with each other. The variation of the fit parameter from both equations were studied relative to the change in the dielectric properties of the mixture of solvents. Standard free energy of transference were comparatively discussed in terms of ion-solvent, ion-ion interactions and the hydration of both the electrolyte and the sugar.

Chemical Phenomena↗
PubMed1997

Pivalates in the selective protection and activation of maltose for the synthesis of sulfated 3-deoxy-maltosyl-(1-->4)-alpha, alpha-trehalose.

Pivaloylation of maltose gave, in satisfactory yield, 1,2,6,2',3',4',6'-hepta-O-pivaloyl-beta-maltose which was converted to the 3-deoxygenated analogue in a Barton-McCombie reaction. 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. After deprotection, the monodeoxygenated tetrasaccharide was sulfated; in the reaction product, one compound fully sulfated at the outer pyranose rings predominated.

Carbohydrate Sequence↗
PubMed2002

The glass transition temperature of mixtures of trehalose and hydroxyethyl starch.

Although mixtures of HES and sugars are used to preserve cells during freezing or drying, little is known about the glass transition of HES, or how mixtures of HES and sugars vitrify. These difficulties may be due to the polydispersity between HES samples or differences in preparation techniques, as well as problems in measuring the glass transition temperature (T(g)) using differential scanning calorimetry (DSC). In this report, we examine the T(g) of mixtures of HES and trehalose sugar with <1% moisture content using DSC measurements. By extrapolating these measurements to pure HES using the Gordon-Taylor and Fox equations, we were able to estimate the T(g) of our HES sample at 44 degrees C. These results were additionally confirmed by using mixtures of glucose-HES which yielded a similar extrapolated T(g) value. Our approach to estimating the glass transition temperature of HES may be useful in other cases where glass transitions are not easily identified.

Calorimetry, Differential Scanning↗