(1S*,2S*,4S*,5S*)-Cyclohexane-1,2,4,5-tetrol monohydrate

Mehta, Goverdhan; Sen, Saikat; Dey, Siddharth S.

doi:10.1107/s0108270105011066

Acta Crystallogr C

2005

DOI: 10.1107/s0108270105011066

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(1S,2S,4S,5S)-Cyclohexane-1,2,4,5-tetrol monohydrate

Goverdhan Mehta

Saikat Sen

Siddharth S. Dey

Abstract: In the title compound, C6H12O4.H2O, 1,4/2,5-cyclohexanetetrol and water molecules are seen to possess twofold symmetry. All four hydroxyl groups of the tetrol participate in extensive intermolecular O-H...O hydrogen bonding to form molecular tapes propagating along the a axis. Translationally related tapes along the c axis are held together by four coordinated water molecules.

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Cited by 5 publications

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“…1963). Some of the structures have been described by mass spectrometry and fewer for the acetylated compounds by gas chromatography–mass spectrometry (GC–MS) (Hudlicky and Cebulak 1993, Mehta et al. 2005).…”

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NITZSCHIA OVALIS(BACILLARIOPHYCEAE) MONO LAKE STRAIN ACCUMULATES 1,4/2,5 CYCLOHEXANETETROL IN RESPONSE TO INCREASED SALINITY¹

Garza-Sánchez

Chapman

Cooper

2009

Journal of Phycology

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The growth of microalgae in hypersaline conditions requires that cells accumulate osmoprotectants. In many instances, these are polyols. We isolated the diatom Nitzschia ovalis H. J. Arn. from the saline and alkaline water body Mono Lake (CA, USA). This isolate can grow in salinities ranging from 5 to 120 parts per thousand (ppt) of salt but normally at 90 ppt salinity. In this report, we identified the major polyol osmoprotectant as 1,4/2,5 cyclohexanetetrol by electron ionization-mass spectrometry (EI-MS), (1) H, (13) C nuclear magnetic resonance spectroscopy (NMR), and infrared (IR) and showed an increase in cellular concentration in response to rising salinity. This increase in the cyclitol concentration was evaluated by gas chromatography of the derived tetraacetylated cyclohexanetetrol obtaining an average of 0.7 fmol · cell(-1) at 5 ppt and rising to 22.5 fmol · cell(-1) at 120 ppt. The 1,4/2,5 cyclohexanetetrol was also detected in the red alga Porphyridium purpureum. Analysis of the free amino acid content in N. ovalis cultures exposed to changes in salinity showed that proline and lysine also accumulate with increased salinity, but the cellular concentration of these amino acids is about 10-fold lower than the concentration of 1,4/2,5 cyclohexanetetrol. The comparison of amino acid concentration per cell with cyclitol suggests that this polyol is important in compensating the cellular osmotic pressure due to increased salinity, but other physiological functions could also be considered.

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mentioning

confidence: 99%

NITZSCHIA OVALIS(BACILLARIOPHYCEAE) MONO LAKE STRAIN ACCUMULATES 1,4/2,5 CYCLOHEXANETETROL IN RESPONSE TO INCREASED SALINITY¹

Garza-Sánchez

Chapman

Cooper

2009

Journal of Phycology

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Crystal Structures of Conformationally Locked Cyclitols: An Analysis of Hydrogen‐Bonded Architectures and their Implications in Crystal Engineering

2007

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A qualitative study has been carried out on selected polycyclitols to evaluate the potential of conformational locking of hydroxy groups in lending predictability to the O–H···O hydrogen‐bonding network observed in the crystal structures of such compounds. The polycyclitols employed in this study are conformationally locked with all the hydroxy groups destined to be axial owing to the trans ring fusion(s) in the polycyclic carbon framework. The consequent formation of intramolecular O–H···O hydrogen bonds between the 1,3‐syn diaxial hydroxy groups now permits any packing pattern in the polycyclitols to be described in terms of a small group of intramolecularly bonded molecular motifs linked to their respective neighbors by four O–H···O bonds. By using this model and the results of CSD analyses of polyols as a guide, the O–H···O hydrogen‐bonded packing motifs most likely to be observed in the crystal structure of each polycyclitol were proposed and compared with those obtained experimentally. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Molecular and Crystal Structure of N-(8-benzylidene-4-phenylhexahydroquinazolin-2(1H)-ylidene)Cyanamide

Sklyar,

Grinev,

Dmitriev

et al. 2024

J Chem Crystallogr

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(1S,2S,4S,5S)-Cyclohexane-1,2,4,5-tetrol monohydrate

Cited by 5 publications

References 16 publications

NITZSCHIA OVALIS(BACILLARIOPHYCEAE) MONO LAKE STRAIN ACCUMULATES 1,4/2,5 CYCLOHEXANETETROL IN RESPONSE TO INCREASED SALINITY¹

NITZSCHIA OVALIS(BACILLARIOPHYCEAE) MONO LAKE STRAIN ACCUMULATES 1,4/2,5 CYCLOHEXANETETROL IN RESPONSE TO INCREASED SALINITY¹

Crystal Structures of Conformationally Locked Cyclitols: An Analysis of Hydrogen‐Bonded Architectures and their Implications in Crystal Engineering

Molecular and Crystal Structure of N-(8-benzylidene-4-phenylhexahydroquinazolin-2(1H)-ylidene)Cyanamide

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(1S*,2S*,4S*,5S*)-Cyclohexane-1,2,4,5-tetrol monohydrate

Cited by 5 publications

References 16 publications

NITZSCHIA OVALIS(BACILLARIOPHYCEAE) MONO LAKE STRAIN ACCUMULATES 1,4/2,5 CYCLOHEXANETETROL IN RESPONSE TO INCREASED SALINITY1

NITZSCHIA OVALIS(BACILLARIOPHYCEAE) MONO LAKE STRAIN ACCUMULATES 1,4/2,5 CYCLOHEXANETETROL IN RESPONSE TO INCREASED SALINITY1

Crystal Structures of Conformationally Locked Cyclitols: An Analysis of Hydrogen‐Bonded Architectures and their Implications in Crystal Engineering

Molecular and Crystal Structure of N-(8-benzylidene-4-phenylhexahydroquinazolin-2(1H)-ylidene)Cyanamide

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(1S,2S,4S,5S)-Cyclohexane-1,2,4,5-tetrol monohydrate

NITZSCHIA OVALIS(BACILLARIOPHYCEAE) MONO LAKE STRAIN ACCUMULATES 1,4/2,5 CYCLOHEXANETETROL IN RESPONSE TO INCREASED SALINITY¹

NITZSCHIA OVALIS(BACILLARIOPHYCEAE) MONO LAKE STRAIN ACCUMULATES 1,4/2,5 CYCLOHEXANETETROL IN RESPONSE TO INCREASED SALINITY¹