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Form II of adipic acid-nicotinohydrazide (1/2).

ABSTRACT: The crystal structure of the title co-crystal, 2C(6)H(7)N(3)O·C(6)H(10)O(4), is a second polymorph, designated form II, of the co-crystal formed between the two mol-ecules [Lemmerer et al. (2011 ?). CrystEngComm, 13, 55-59]. The asymmetric unit comprises one mol-ecule of nicotinic acid hydrazide, and one half-mol-ecule of adipic acid (the entire mol-ecule is completed by the application of a centre of inversion). In the crystal, mol-ecules assemble into a three-dimensional network of hydrogen bonds, formed by three N-H?O hydrogen bonds and one O-H?N hydrogen bond. The O-H?N hydrogen bond formed between the carboxyl group and the pyridine ring is supported by a C-H?O hydrogen bond.

SUBMITTER: Lemmerer A

PROVIDER: S-EPMC3254528 | biostudies-literature | 2012 Jan

REPOSITORIES: biostudies-literature

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Form II of adipic acid-nicotinohydrazide (1/2).

Lemmerer Andreas A Bernstein Joel J Kahlenberg Volker V

Acta crystallographica. Section E, Structure reports online 20111221 Pt 1

The crystal structure of the title co-crystal, 2C(6)H(7)N(3)O·C(6)H(10)O(4), is a second polymorph, designated form II, of the co-crystal formed between the two mol-ecules [Lemmerer et al. (2011 ▶). CrystEngComm, 13, 55-59]. The asymmetric unit comprises one mol-ecule of nicotinic acid hydrazide, and one half-mol-ecule of adipic acid (the entire mol-ecule is completed by the application of a centre of inversion). In the crystal, mol-ecules assemble into a three-dimensional network of hydrogen bo ...[more]

PMID: 22259474

Similar Datasets

Urea-adipic acid (2/1).

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Nicotinohydrazide.

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| S-EPMC2915351 | biostudies-literature

Nicotinohydrazide.

Project description:IN THE TITLE COMPOUND (ALTERNATIVE NAME: pyridine-3-carbo-hydrazide, C(6)H(7)N(3)O), the asymmetric unit contains a single mol-ecule. In contrast with nicotinic acid and nicotinamide, the C=O bond is found to be oriented cis with respect to the C(ipso) C N fragment in the pyridine ring. The pyridine ring and the hydrazide group make a dihedral angle of 34.0 (2)°. In the crystal structure, mol-ecules are associated into a three-dimensional framework by a combination of N-H⋯N and three-centre N-H⋯O hydrogen bonds.

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Accessing Mefenamic Acid Form II through High-Pressure Recrystallisation.

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Fully biological production of adipic acid analogs from branched catechols.

Project description:Microbial production of adipic acid from lignin-derived monomers, such as catechol, is a greener alternative to the petrochemical-based process. Here, we produced adipic acid from catechol using catechol 1,2-dioxygenase (CatA) and a muconic acid reductase (MAR) in Escherichia coli. As the reaction progressed, the pH of the media dropped from 7 to 4-5 and the muconic acid isomerized from the cis,cis (ccMA) to the cis,trans (ctMA) isomer. Feeding experiments suggested that cells preferentially uptook ctMA and that MAR efficiently reduced all muconic isomers to adipic acid. Intrigued by the substrate promiscuity of MAR, we probed its utility to produce branched chiral diacids. Using branched catechols likely found in pretreated lignin, we found that while MAR fully reduced 2-methyl-muconic acid to 2-methyl-adipic acid, MAR reduced only one double bond in 3-substituted muconic acids. In the future, MAR's substrate promiscuity could be leveraged to produce chiral-branched adipic acid analogs to generate branched, nylon-like polymers with reduced crystallinity.

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Supra-molecular architecture in a co-crystal of the N(7)-H tautomeric form of N (6)-benzoyl-adenine with adipic acid (1/0.5).

Project description:The asymmetric unit of the title co-crystal, C12H9N5O·0.5C6H10O4, consists of one mol-ecule of N (6)-benzoyl-adenine (BA) and one half-mol-ecule of adipic acid (AA), the other half being generated by inversion symmetry. The dihedral angle between the adenine and phenyl ring planes is 26.71 (7)°. The N (6)-benzoyl-adenine mol-ecule crystallizes in the N(7)-H tautomeric form with three non-protonated N atoms. This tautomeric form is stabilized by intra-molecular N-H⋯O hydrogen bonding between the carbonyl (C=O) group and the N(7)-H hydrogen atom on the Hoogsteen face of the purine ring, forming an S(7) ring motif. The two carboxyl groups of adipic acid inter-act with the Watson-Crick face of the BA mol-ecules through O-H⋯N and N-H⋯O hydrogen bonds, generating an R 2 (2)(8) ring motif. The latter units are linked by N-H⋯N hydrogen bonds, forming layers parallel to (10-5). A weak C-H⋯O hydrogen bond is also present, linking adipic acid mol-ecules in neighbouring layers, enclosing R (2) 2(10) ring motifs and forming a three-dimensional structure. C=O⋯π and C-H⋯π inter-actions are also present in the structure.

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A yeast chemogenomic screen identifies pathways that modulate adipic acid toxicity.

Project description:Adipic acid production by yeast fermentation is gaining attention as a renewable source of platform chemicals for making nylon products. However, adipic acid toxicity inhibits yeast growth and fermentation. Here, we performed a chemogenomic screen in Saccharomyces cerevisiae to understand the cellular basis of adipic acid toxicity. Our screen revealed that KGD1 (a key gene in the tricarboxylic acid cycle) deletion improved tolerance to adipic acid and its toxic precursor, catechol. Conversely, disrupting ergosterol biosynthesis as well as protein trafficking and vacuolar transport resulted in adipic acid hypersensitivity. Notably, we show that adipic acid disrupts the Membrane Compartment of Can1 (MCC) on the plasma membrane and impacts endocytosis. This was evidenced by the rapid internalization of Can1 for vacuolar degradation. As ergosterol is an essential component of the MCC and protein trafficking mechanisms are required for endocytosis, we highlight the importance of these cellular processes in modulating adipic acid toxicity.

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Bis(2,6-diamino-pyridinium)-adipate-adipic acid-water (2/1/1/2).

Project description:The crystal structure of the title compound, 2C(5)H(8)N(3) (+)·C(6)H(8)O(4) (2-)·C(6)H(10)O(4)·2H(2)O, consists of amino-pyridinium cations, adipate dianions, adipic acid mol-ecules and disordered solvent water mol-ecules [occupancies 0.50 (4) and 0.50 (4)]. Both the adipate and adipic acid are located across inversion centres. Eight-membered hydrogen-bonded rings exist involving amino-pyridinium and adipate ions. Adipic acid mol-ecules and adipate anions are linked into zigzag supra-molecular chains by O-H⋯O hydrogen bonds.

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Adipic acid-2,6-bis-(1H-benzimidazol-2-yl)pyridine-water (1/2/4).

Project description:The asymmetric unit of the title hydrated co-crystal, 2C19H13N5·C6H10O4·4H2O, consists of one 2,6-bis-(1H-benzimidazol-2-yl)pyridine mol-ecule, half of an adipic acid mol-ecule (bis-ected by an inversion center) and two water solvates. In the crystal, N-H?O, O-H?O and O-H?N hydrogen bonds and ?-? inter-actions [centroid-centroid distances = 3.769?(2) and 3.731?(2)?Å] form a three-dimensional supra-molecular structure.

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Biocatalytic production of adipic acid from glucose using engineered <i>Saccharomyces cerevisiae</i>.

Project description:Adipic acid is an important industrial chemical used in the synthesis of nylon-6,6. The commercial synthesis of adipic acid uses petroleum-derived benzene and releases significant quantities of greenhouse gases. Biocatalytic production of adipic acid from renewable feedstocks could potentially reduce the environmental damage and eliminate the need for fossil fuel precursors. Recently, we have demonstrated the first enzymatic hydrogenation of muconic acid to adipic acid using microbial enoate reductases (ERs) - complex iron-sulfur and flavin containing enzymes. In this work, we successfully expressed the Bacillus coagulans ER in a Saccharomyces cerevisiae strain producing muconic acid and developed a three-stage fermentation process enabling the synthesis of adipic acid from glucose. The ability to express active ERs and significant acid tolerance of S. cerevisiae highlight the applicability of the developed yeast strain for the biocatalytic production of adipic acid from renewable feedstocks.

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