The crystal and molecular structure of methyl β-cellobioside–methanol

Ham, Jimin; Williams, Dale G.

doi:10.1107/s0567740870004132

Cited by 131 publications

(52 citation statements)

References 4 publications

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“…than those in the ring in agreement with the observation of Ham & Williams (1970). The exocyclic C-O distances excluding the anomeric and bridge C-O bonds range from 1.424 to 1.427 ,/k, averaging 1.425 A.…”

Section: The Crystal and Molecular Structure Of A-maltosesupporting

confidence: 77%

“…A similar trend was observed in methyl fl-maltopyranoside , /]-lactose (Hirotsu & Shimada, 1974), and fl-cellobiose (Chu & Jeffrey, 1968). However, in methyl fl-ceUobioside (Ham & Williams, 1970), these distances are nearly equal (< la) in both rings. In a-lactose (Fries, Rao & Sundaralingam, 1971), the same pattern of C(1)-O(5) < C(5)-O(5) is found for the unprimed ring, while the reverse trend C(l')-O(5') > C(5')-O(5'), is found in the primed ring.…”

Section: The Crystal and Molecular Structure Of A-maltosementioning

confidence: 98%

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The crystal and molecular structure of α-maltose

Takusagawa¹,

Jacobson²

1978

Acta Crystallogr Sect B

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The crystal structure of (t-maltose [4-O-qt-D-glucopyranosyl)-~vD-glucopyranose] has been determined by single-crystal X-ray techniques. The unit cell is orthorhombic, space group P2z2~2 ~, with dimensions a = 12.667 (3), b = 13.830 (5) and c = 8.400 (2) A. The structure was solved using a direct method and refined by full-matrix least-squares procedures. Difference syntheses showed all H atoms and also indicated a partial (18%) random substitution of tt-maltose molecules by the fl anomer. The final discrepancy factor, R, is 0.043 for 1379 observed reflections. Bond lengths and angles are in good agreement with those of other disaccharides. The pyranosyl rings are slightly distorted from the C1 chair form and the O(1)-O(4) distance of 4.052 A is shorter than found previously. The primary alcohol groups have gauche-trans orientations. All the O atoms in both the t~ and fl anomers, except the bridge O atoms, take part in a hydrogen-bonding network. 213 Introduction ExperimentalIn connection with X-ray diffraction studies of selected carbohydrates in this laboratory (James, French & Rundle, 1959;Hybl, Rundle & Williams, 1965;Jacobson, Wunderlich & Lipscomb, 1961;Hackert & Jacobson, 1971), we have determined the crystal and molecular structure of st-maltose. Maltose is obtained, along with other products, from the partial hydrolysis of starch in aqueous acidic solution. Maltose is also formed in the fermentation of starch to ethyl alcohol, when catalyzed by the enzyme diastase, which is present in malt. The i.mportance of the molecular conformations of carbohydrates has long been recognized, and therefore a number of crystal investigations of monosaccharides, disaccharides, polysaccharides and their derivatives have been carried out using X-ray and neutron diffraction techniques. Just as the molecular structure of cellobiose is important in order to better understand the properties and reactions of cellulose, the molecular conformation of maltose is important in basic studies of starch. The crystal structures of fl-maltose monohydrate (Quigley, Sarko & Marchessault, 1970), methyl fl-maltopyranoside monohydrate , and isomaltose monohydrate (Dreissig & Luger, 1973) have been determined by other workers. We decided to carry out a molecular structure investigation of a-maltose in order to elucidate its molecular conformation and to compare the st and fl forms and the corresponding hydrogen bonding in these solids. Crystalline samples of it-maltose containing approximately 20% of the fl anomer and whose preparation has been described by Hodge, Rendleman & Nelson (1972) were kindly supplied by J. E. Hodge and D. French. The unit-ceU parameters and their estimated standard deviations were obtained by a leastsquares fit to the +20 values of 12 independent highangle reflections.For data collection a crystal in the shape of a parallelepiped formed with the (100), (010) and (001) planes as faces and of dimensions 0.3 × 0.3 × 0.5 mm was selected. Data were collected at room temperature using an automated four-circle diffracto...

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Section: The Crystal and Molecular Structure Of A-maltosesupporting

confidence: 77%

Section: The Crystal and Molecular Structure Of A-maltosementioning

confidence: 98%

The crystal and molecular structure of α-maltose

Takusagawa¹,

Jacobson²

1978

Acta Crystallogr Sect B

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“…There is no direct intramolecular hydrogen bonding such as is found in sucrose (Brown & Levy, 1963), cellobiose (Chu & Jeffrey, 1968), methyl-fl-cellobioside-methanol (Ham & Williams, 1970), p-maltose monohydrate (Quigley, Sarko & Marchessault, 1971), methyl-fl-maltoside monohydrate (Chu & Jeffrey, 1967), and fl-lactose monohydrate (Fries, Rao & Sundaralingam, 1971). However, water molecule W(1) is linked by hydrogen bonding both to 0(2) and to O'(4), and molecule W(2) is linked both to 0(2) and to O'(6), all within the same trehalose molecule.…”

Section: Discussionmentioning

confidence: 99%

The crystal structure of α,α-trehalose dihydrate from three independent X-ray determinations

Brown¹,

Rohrer²,

Berking³

et al. 1972

Acta Crystallogr B Struct Crystallogr Cryst Chem

148

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The structure of the dihydrate of the nonreducing disaccharide a,a-trehalose (a-D-glucopyranosyl a-D-glucopyranoside) has been determined independently by direct methods in three different laboratories. There are four units C~2H22Ol~.2H20 in an orthorhombic cell (P212a2a) with a= 12"230 (2), Comparison of coordinates suggests that their standard errors may have been underestimated by a factor of ~2. The a,a-trehalose molecule has approximate C2 symmetry, but there are some significant structural differences between the two chemically equivalent halves. The angles at the ring oxygen atoms are 114-0 and 114-2°; the angle at the glycosidic oxygen is 115.8 °. The two rings have Cl conformations; the conformations about the linking C-O bonds are stabilized by the conformational 6anomeric effect' and also by a complex system of hydrogen bonds involving all of the hydroxyl groups, both water molecules, and one ring oxygen. By hydrogen bonding each glucopyranosy] moiety is linked to the other in the same molecule indirectly through two different water molecules. The helical arrangement of hydrogen bonds about the screw axes parallel to e suggests the possibility of observing ferroelectric behavior.

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“…The conformation of the xylobiose residue of the trisaccharide was of interest because it could be compared to the minimum energy conformation position defined by potential energy functions for a xylobiose disaccharide (Sundararajan & Rao, 1969). In addition, the orientation of the two rings could also be compared to the conformation of the other/~-l,4-linked disaccharide structures, cellobiose (Chu & Jeffrey, 1968), methyl ,8-cellobioside (Ham & Williams, 1970), and a-lactose (Fries, Rao & Sundaralingam, 1971), all of which contain an intramoleculal hydrogen bond between 0(3') and 0(5). An examination of the orientation of the 4-O-methyl-o-glucuronic acid ring with respect to the xylobiose backbone was also of interest in that it could provide some information as to how this ring might be oriented in the polymer as a single branched unit.…”

Section: Introductionmentioning

confidence: 99%