5-O-Acetyl-d-ribono-1,4-lactone

Bortoluzzi, A.J.; Sebrão, D.; Sá, M.M.; Nascimento, M.G.

doi:10.1107/S1600536811038670

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2778

https://doi.org/10.1107/S1600536811038670

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5-O-Acetyl-D-ribono-1,4-lactone

Adailton J. Bortoluzzi,^a ^* Damianni Sebrão,^a Marcus M. Sá ^a and M. G. Nascimento ^a

^aDepto. de Química - UFSC, 88040-900 - Florianópolis, SC, Brazil
^*Correspondence e-mail: adajb@qmc.ufsc.br

(Received 6 August 2011; accepted 20 September 2011; online 30 September 2011)

The title compound, C₇H₁₀O₆, was obtained from a regioselective enzyme-catalysed acylation of D-ribono-1,4-lactone. The five-membered ring of the acylated sugar shows an envelope conformation. In the crystal, the molecules are linked by intermolecular O—H⋯O hydrogen-bonds, forming a one-dimensional polymeric structure parallel to [010]. In addition, packing analysis shows stacking along the b axis.

Related literature

For general background to carbohydrates, see: Corma et al. (2007 ); Han et al. (1993 ); Simone et al. (2005 ). For biocatalysed acylation reactions, see: Díaz-Rodríguez et al. (2005 ); Wu et al. (2008 ). For related structures, see: Shalaby et al. (1994 ); Bye (1979 ); Amador et al. (2004 ); Sá et al. (2008 ); Gress & Jeffrey (1976 ).

Experimental

Crystal data

C₇H₁₀O₆
M_r = 190.15
Monoclinic, P 2₁
a = 6.1409 (4) Å
b = 5.1952 (15) Å
c = 13.1844 (18) Å
β = 95.118 (12)°
V = 418.95 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 293 K
0.50 × 0.30 × 0.13 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
2164 measured reflections
1346 independent reflections
1015 reflections with I > 2σ(I)
R_int = 0.046
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.135
S = 1.07
1346 reflections
127 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4ⁱ	0.85 (5)	1.95 (5)	2.781 (3)	164 (3)
O4—H4⋯O2ⁱ	0.85 (5)	2.15 (5)	2.910 (3)	148 (5)
O4—H4⋯O3ⁱ	0.85 (5)	2.41 (6)	3.086 (4)	136 (4)
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+1]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: SET4 in CAD-4 Software; data reduction: HELENA (Spek, 1996 ); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811038670/lr2026sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811038670/lr2026Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811038670/lr2026Isup3.mol

checkCIF report

Comment top

Carbohydrates are valuable sources for the production of synthetic compounds of general relevance (Corma et al., 2007). D-Ribono-1,4-lactone (1) is an inexpensive and abundant sugar derivative that is commercially available from renewable resources (Han et al., 1993, Simone et al., 2005). Many synthetic transformations involving 1 lead to unexpected processes ranging from rearrangements to functional group migrations. In such cases, single-crystal X-ray analysis is the only reliable method for the correct structural and conformational assignments (Sá et al., 2008). Enzyme-catalyzed acylation of sugars is, in general, regioselective. Lipases (EC 3.1.1.3) are the most used biocatalyst for this purpose, especially Candida antarctica lipase B - CAL-B (Díaz-Rodríguez et al., 2005; Wu et al., 2008). We describe herein the crystal structure of 5-O-acetyl-D-ribono-1,4-lactone (2), synthesized from the regioselective acetylation of 1 using CAL-B (Fig. 1).

The molecular structure of the title compound exhibits its 1,4-lactone ring with envelope conformation, which is enveloped on C3 (Fig. 2). Hydroxyl groups are involved in different types of intermolecular O—H···O hydrogen-bonds (Table 1). Hydroxyl group (O3) is the donor for linear hydrogen-bond (O3—H3···O4), whereas hydroxyl group (O4) is the donor for bifurcated interactions (O4—H4···O2 and O4—H4···O3). These interactions link molecules forming one-dimensional zigzag infinite chain parallel to [010] direction. Also, packing analysis shows stack along the b crystallographic axis (Fig. 3).

Related literature top

For general background to carbohydrates, see: Corma et al. (2007); Han et al. (1993); Simone et al. (2005). For biocatalysed acylation reactions, see: Díaz-Rodríguez et al. (2005); Wu et al. (2008). For related structures, see: Shalaby et al. (1994); Bye (1979); Amador et al. (2004); Sá et al. (2008); Gress & Jeffrey (1976).

Experimental top

The reaction was initiated by dissolving D-ribono-1,4-lactone (74.0 mg, 0.5 mmol) and vinyl acetate (0.14 ml, 1.5 mmol) in anhydrous acetonitrile (10.0 ml) followed by the addition of CAL-B (10.0 mg, Novozym 435, 10,000 PLU/g). The mixture was shaken at 308 K and 150 rpm for 24 h. The reaction was stopped by filtering off the lipase. Finally, solvent was evaporated and the product 5-O-acetyl-D-ribono-1,4-lactone was obtained as a white solid (94% yield). Careful recrystallization from acetone provided the crystals (413–414 K) suitable for X-ray diffraction analysis.

Structure description top

For general background to carbohydrates, see: Corma et al. (2007); Han et al. (1993); Simone et al. (2005). For biocatalysed acylation reactions, see: Díaz-Rodríguez et al. (2005); Wu et al. (2008). For related structures, see: Shalaby et al. (1994); Bye (1979); Amador et al. (2004); Sá et al. (2008); Gress & Jeffrey (1976).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: SET4 in CAD-4 Software (Enraf–Nonius, 1989); data reduction: HELENA (Spek, 1996); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Biocatalyzed acylation reaction.
	Fig. 2. The molecular structure of enantiomeric pair of the title compound showing the atom-labelling scheme. Ellipsoids are drawn at the 40% probability level.
	Fig. 3. Partial packing of the title compound showing hydrogen bonds.

5-O-Acetyl-D-ribono-1,4-lactone top

Crystal data top

C₇H₁₀O₆	F(000) = 200
M_r = 190.15	D_x = 1.507 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 6.1409 (4) Å	θ = 3.5–20.5°
b = 5.1952 (15) Å	µ = 0.13 mm⁻¹
c = 13.1844 (18) Å	T = 293 K
β = 95.118 (12)°	Prismatic, colorless
V = 418.95 (14) Å³	0.50 × 0.30 × 0.13 mm
Z = 2

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.046
Radiation source: fine-focus sealed tube	θ_max = 30.0°, θ_min = 1.6°
Graphite monochromator	h = −8→8
ω–2θ scans	k = −7→2
2164 measured reflections	l = −18→2
1346 independent reflections	3 standard reflections every 200 reflections
1015 reflections with I > 2σ(I)	intensity decay: 1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0807P)² + 0.0065P] where P = (F_o² + 2F_c²)/3
1346 reflections	(Δ/σ)_max < 0.001
127 parameters	Δρ_max = 0.29 e Å⁻³
1 restraint	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₇H₁₀O₆	V = 418.95 (14) Å³
M_r = 190.15	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 6.1409 (4) Å	µ = 0.13 mm⁻¹
b = 5.1952 (15) Å	T = 293 K
c = 13.1844 (18) Å	0.50 × 0.30 × 0.13 mm
β = 95.118 (12)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.046
2164 measured reflections	3 standard reflections every 200 reflections
1346 independent reflections	intensity decay: 1%
1015 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.047	1 restraint
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.29 e Å⁻³
1346 reflections	Δρ_min = −0.18 e Å⁻³
127 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.4264 (4)	−0.0865 (5)	0.32056 (19)	0.0355 (5)
C2	0.4464 (4)	0.1808 (5)	0.3674 (2)	0.0344 (5)
H2	0.4839	0.3062	0.3162	0.041*
C3	0.2154 (4)	0.2326 (5)	0.3976 (2)	0.0364 (6)
H3A	0.1774	0.4155	0.3913	0.044*
C4	0.0742 (4)	0.0687 (6)	0.3213 (2)	0.0405 (6)
H4A	−0.0460	−0.0050	0.3559	0.049*
C5	−0.0206 (5)	0.2048 (8)	0.2270 (2)	0.0507 (8)
H5A	−0.1029	0.0850	0.1820	0.061*
H5B	−0.1181	0.3413	0.2448	0.061*
C6	0.1100 (5)	0.5012 (7)	0.1095 (2)	0.0482 (7)
C7	0.3079 (6)	0.5894 (10)	0.0629 (3)	0.0660 (11)
H7A	0.3294	0.4848	0.0046	0.099*
H7B	0.4329	0.5748	0.1118	0.099*
H7C	0.2895	0.7658	0.0422	0.099*
O1	0.2157 (3)	−0.1406 (4)	0.29314 (16)	0.0433 (5)
O2	0.5706 (3)	−0.2355 (4)	0.30942 (17)	0.0480 (5)
O3	0.6139 (3)	0.1709 (5)	0.44808 (17)	0.0449 (5)
O4	0.1877 (3)	0.1377 (5)	0.49711 (16)	0.0445 (5)
O5	0.1590 (3)	0.3103 (5)	0.17745 (16)	0.0482 (6)
O6	−0.0705 (4)	0.5837 (6)	0.0916 (2)	0.0666 (8)
H3	0.661 (6)	0.325 (9)	0.455 (3)	0.047 (10)*
H4	0.265 (7)	0.229 (12)	0.540 (4)	0.070 (14)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0392 (12)	0.0292 (12)	0.0375 (12)	−0.0038 (11)	0.0002 (10)	0.0020 (11)
C2	0.0301 (10)	0.0282 (12)	0.0445 (13)	−0.0040 (10)	0.0004 (9)	0.0007 (11)
C3	0.0332 (11)	0.0304 (14)	0.0452 (13)	0.0003 (10)	0.0004 (9)	−0.0002 (11)
C4	0.0320 (11)	0.0398 (16)	0.0489 (14)	−0.0059 (12)	−0.0006 (10)	0.0034 (13)
C5	0.0368 (12)	0.060 (2)	0.0535 (16)	−0.0001 (15)	−0.0068 (11)	0.0076 (17)
C6	0.0556 (16)	0.0446 (16)	0.0417 (14)	0.0035 (16)	−0.0107 (12)	−0.0012 (14)
C7	0.068 (2)	0.078 (3)	0.0513 (18)	−0.002 (2)	0.0015 (16)	0.015 (2)
O1	0.0416 (9)	0.0331 (10)	0.0535 (11)	−0.0079 (9)	−0.0054 (8)	−0.0032 (9)
O2	0.0480 (11)	0.0389 (12)	0.0566 (12)	0.0027 (10)	0.0018 (9)	−0.0052 (10)
O3	0.0371 (9)	0.0401 (13)	0.0555 (12)	−0.0052 (10)	−0.0078 (8)	−0.0051 (10)
O4	0.0411 (9)	0.0487 (13)	0.0438 (10)	0.0013 (10)	0.0033 (8)	−0.0021 (10)
O5	0.0429 (10)	0.0534 (14)	0.0478 (11)	0.0049 (10)	0.0014 (8)	0.0081 (11)
O6	0.0569 (13)	0.0666 (18)	0.0728 (15)	0.0090 (13)	−0.0140 (11)	0.0155 (15)

Geometric parameters (Å, º) top

C1—O2	1.195 (3)	C5—O5	1.439 (4)
C1—O1	1.342 (3)	C5—H5A	0.9700
C1—C2	1.521 (4)	C5—H5B	0.9700
C2—O3	1.413 (3)	C6—O6	1.192 (4)
C2—C3	1.531 (4)	C6—O5	1.352 (4)
C2—H2	0.9800	C6—C7	1.482 (5)
C3—O4	1.425 (4)	C7—H7A	0.9600
C3—C4	1.528 (4)	C7—H7B	0.9600
C3—H3A	0.9800	C7—H7C	0.9600
C4—O1	1.460 (4)	O3—H3	0.85 (5)
C4—C5	1.502 (4)	O4—H4	0.85 (5)
C4—H4A	0.9800

O2—C1—O1	122.6 (3)	C3—C4—H4A	108.5
O2—C1—C2	127.4 (2)	O5—C5—C4	107.4 (2)
O1—C1—C2	110.0 (2)	O5—C5—H5A	110.2
O3—C2—C1	107.4 (2)	C4—C5—H5A	110.2
O3—C2—C3	116.1 (2)	O5—C5—H5B	110.2
C1—C2—C3	102.9 (2)	C4—C5—H5B	110.2
O3—C2—H2	110.0	H5A—C5—H5B	108.5
C1—C2—H2	110.0	O6—C6—O5	122.9 (3)
C3—C2—H2	110.0	O6—C6—C7	126.1 (3)
O4—C3—C4	107.8 (2)	O5—C6—C7	111.0 (3)
O4—C3—C2	111.6 (2)	C6—C7—H7A	109.5
C4—C3—C2	102.4 (2)	C6—C7—H7B	109.5
O4—C3—H3A	111.5	H7A—C7—H7B	109.5
C4—C3—H3A	111.5	C6—C7—H7C	109.5
C2—C3—H3A	111.5	H7A—C7—H7C	109.5
O1—C4—C5	109.6 (3)	H7B—C7—H7C	109.5
O1—C4—C3	105.5 (2)	C1—O1—C4	110.9 (2)
C5—C4—C3	116.0 (3)	C2—O3—H3	105 (2)
O1—C4—H4A	108.5	C3—O4—H4	108 (3)
C5—C4—H4A	108.5	C6—O5—C5	116.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4ⁱ	0.85 (5)	1.95 (5)	2.781 (3)	164 (3)
O4—H4···O2ⁱ	0.85 (5)	2.15 (5)	2.910 (3)	148 (5)
O4—H4···O3ⁱ	0.85 (5)	2.41 (6)	3.086 (4)	136 (4)

Symmetry code: (i) −x+1, y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₇H₁₀O₆
M_r	190.15
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	6.1409 (4), 5.1952 (15), 13.1844 (18)
β (°)	95.118 (12)
V (Å³)	418.95 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.50 × 0.30 × 0.13

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2164, 1346, 1015
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.135, 1.07
No. of reflections	1346
No. of parameters	127
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.18

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), SET4 in CAD-4 Software (Enraf–Nonius, 1989), HELENA (Spek, 1996), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4ⁱ	0.85 (5)	1.95 (5)	2.781 (3)	164 (3)
O4—H4···O2ⁱ	0.85 (5)	2.15 (5)	2.910 (3)	148 (5)
O4—H4···O3ⁱ	0.85 (5)	2.41 (6)	3.086 (4)	136 (4)

Symmetry code: (i) −x+1, y+1/2, −z+1.

Acknowledgements

The authors thank the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES), the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) and the Financiadora de Estudos e Projetos (FINEP) for financial support.

References

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