Structure of difructose anhydride III (difructofuranose 1,2',2,3'-anhydride)

Mcdonald, Emma J; Jackson, R F W

doi:10.6028/jres.024.007

Cited by 30 publications

(11 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Among these inulin products, DFA III, which consists of two fructose molecules with two reciprocal glycosidic linkages, has attracted increasing attention from the scientific and commercial community because of its promising physiological functions. For example, due to its low calories (52% sweetness but only 1 / 15 of the energy of sucrose), it can be used as an ideal sucrose substitute.…”

Section: Introductionmentioning

confidence: 99%

“…For inulin, it involves β-fructofuranosidase (EC 3.2.1.26) 14 and exoinulinase (EC 3.2.1.7), 15 which hydrolyze inulin into fructose; endoinulinase (EC 3.2.1.7), 16 which converts inulin into fructo-oligosaccharides; and inulin fructotransferases (IFTases), which decompose inulin into di-D-fructofuranose 1,2′:2,1′ dianhydride (difructose anhydride I, DAF I) (EC 4.2.2.17 for DFA I-forming IFTase) 17 or di-Dfructofuranose 1,2′:2,3′ dianhydride (difructose anhydride III, DAF III) (EC 4.2.2.18 for DFA III-forming IFTase). 18,19 Among these inulin products, DFA III, which consists of two fructose molecules with two reciprocal glycosidic linkages, 20 has attracted increasing attention from the scientific and commercial community because of its promising physiological functions. For example, due to its low calories (52% sweetness but only 1 / 15 of the energy of sucrose), 21 it can be used as an ideal sucrose substitute.…”

Section: ■ Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Probing the Role of Two Critical Residues in Inulin Fructotransferase (DFA III-Producing) Thermostability from Arthrobacter sp. 161MFSha2.1

Wang

Zhang

et al. 2016

J. Agric. Food Chem.

View full text Add to dashboard Cite

Inulin fructotransferase (IFTase) is an important enzyme that produces di-d-fructofuranose 1,2':2,3' dianhydride (DAF III), which is beneficial for human health. Present investigations mainly focus on screening and characterizing IFTase, including catalytic efficiency and thermostability, which are two important factors for enzymatic industrial applications. However, few reports aimed to improve these two characteristics based on the structure of IFTase. In this work, a structural model of IFTase (DFA III-producing) from Arthrobacter sp. 161MFSha2.1 was constructed through homology modeling. Analysis of this model reveals that two residues, Ser-309 and Ser-333, may play key roles in the structural stability. Therefore, the functions of the two residues were probed by site-directed mutagenesis combined with the Nano-DSC method and assays for residual activity. In contrast to other mutations, single mutation of serine 309 (or serine 333) to threonine did not decrease the enzymatic stability, whereas double mutation (serine 309 and serine 333 to threonine) can enhance thermostability (by approximately 5 °C). The probable mechanisms for this enhancement were investigated.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Probing the Role of Two Critical Residues in Inulin Fructotransferase (DFA III-Producing) Thermostability from Arthrobacter sp. 161MFSha2.1

Wang

Zhang

et al. 2016

J. Agric. Food Chem.

View full text Add to dashboard Cite

show abstract

“…T h e acetyl groups in IV were believed (14) t o be a t the 3-, 3'-, 4-, and 4'-positions. This conclusion was substantiated in the present investigation by tosylation of IV followed by reaction with sodium iodide t o form a tetra-0-acetyl-6,G1-dideoxydiiodo derivative of 11.…”

Section: In Chloroform: ( a ) "Di-d-fr~~ctose Anhydride I" Hexaacetatmentioning

confidence: 99%

THE CONFIGURATION AND CONFORMATION OF "DI-D-FRUCTOSE ANHYDRIDE I"

Lemieux¹,

Ramakrishnan²

1964

Can. J. Chem.

View full text Add to dashboard Cite

"Di-D-fructose anhydride I", obtained by acid depolymerization of inulin triacetate, was found t o be 1',2-anhydro-[l-(a-~-fructofuranosyl)-~ctofuranose]. The high resistance t o oxidation by periodate found for the a-D-fructofuranoside portion was related t o the conformation for the ring wherein the 3'-and 4'-hydroxyl groups are in quasi-axial orientation. This and other conclusions about the conformations of the anhydride were based on a cornparison of the 100 Mc.p.s. proton inagnetic resonance spectra of the 6,6'-dideoxytetra-0-acetyl derivative of the anhydride, sucrose octaacetate, and 1,6-anhydro-a-D-galactofura~lose triacetate. DISCUSSIONWhen D-fructose reacts with aqueous acid, dimeric D-fructose anhydrides are formed which possess a central 1,4-dioxane ring. Six such di-D-fructose dianhydrides have been described (I). Although both the action of aqueous acid on D-fructose (2) or inulin (3) and the heating of a concentrated aqueous solution of D-fructose (4, 5 ) lead to mixtures of these anhydrides, the treatment of inulin triacetate in chloroform with fuming nitric acid yields only the hexaacetate of that isomer known as "di-D-fructose anhydride I" (6). The formation of the di-D-fructose anhydrides has been attributed (7,8) to the stability of the 1,4-dioxane ring."Di-D-fructose anhydride I" was first reported allnost simultaneously by Jackson and Goergen (3) and by Irvine and Stevenson (6). Methylation followed by hydrolysis to yield 3,4,6-tri-0-methyl-D-fructose established the con~pound to be the 1,2':lf,2-dianhydride of D-fructose (7). The consumption of 2 moles of periodic acid by the con~pound provided additional support for this structure (9). The configurations of the anomeric centers in the di-D-fructose anhydrides have not been established.The alp-configuration was readily established for "di-D-fructose anhydride I" by application of proton magnetic resonance (NMR) spectroscopy. T o achieve better chemical shifts between the various lcinds of protons, the spectrum of the hexa-0-acetyl derivative (I) of I1 was determined a t 100 Mc.p.s. with chlorofornl as solvent. Should the compound contain either the a,a-or p,p-configurations, the conformational equilibration would be expected to lead to time-averaging of the resonances for the protons a t the corresponding positions in each of the rings. Certainly, the chemical shifts of the protons a t the 1-and 1'-positions would be averaged out through rapid conformational change of the dioxane ring (10). This would result in the averaging of the resonances for protons a t corresponding positions in the furanoside rings even though these rings should be conformationally rigid. Therefore, the N M R spectra for the 1,2':1',2-di-D-fructofuranose anhydride hexaacetates with the a,a-and P,P-configurations should show signals for only five ltinds of protons on the sugar residue and three pairs of nonequivalent acetyl groups. However, as seen from the spectrum in Fig. 1, the hexaacetate (1) of "di-D-fructose anhydride I" (11) provided a much more comp...

show abstract

“…If a-or fl-D-fructopyranose is dentoed by a-or /3-D-Fp and re-or /3-D-fructofuranose by a-or fl-D-Ff these 1,2':2,1'-dianhydrides are, in abbreviated form, a-D-Fp-/3-D-Fp (diheterolevulosan I), a-D-Ff-fl-D-Fp (diheterolevulsan II), fl-D-Ff-fl-D-Fp (diheterolevulosan III), fl-D-Fp-fl-D-Fp (diheterolevulosan IV) and a-D-Ff-fl-D-Ff (the so-called difructose dianhydride I, Irvine & Stevenson, i929;McDonald & Jackson, 1940).…”

Section: And Joop H Van Der Maas and Bert Lutzmentioning

confidence: 99%