Heterocycles derived from the condensation of aliphatic diamines with succinic and glutaric acid derivatives

Grinberg, Horacio; Lamdan, Sámuel; Gaozza, Carlos H.

doi:10.1002/jhet.5570120430

Cited by 12 publications

(4 citation statements)

References 3 publications

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“…DapD was prepared and crystallized as described (Binder et al 1996). The succinamide‐CoA cofactor analog was prepared from N ‐(2‐aminoethyl)‐succinamic acid (Grinberg et al 1975) by reaction with an enzymatically prepared CoA analog synthon, as described (Martin et al 1994). Crystals of DapD in complex with pimelate and succinyl‐CoA were prepared by cocrystallization using the hanging drop vapor diffusion method.…”

Section: Methodsmentioning

confidence: 99%

Acyl group specificity at the active site of tetrahydridipicolinate N‐succinyltransferase

et al. 2002

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Tetrahydrodipicolinate N-succinyltransferase (DapD) catalyzes the succinyl-CoA-dependent acylation of L-2-amino-6-oxopimelate to 2-N-succinyl-6-oxopimelate as part of the succinylase branch of the meso-diaminopimelate/lysine biosynthetic pathway of bacteria, blue-green algae, and plants. This pathway provides meso-diaminopimelate as a building block for cell wall peptidoglycan in most bacteria, and is regarded as a target pathway for antibacterial agents. We have solved the X-ray crystal structures of DapD in ternary complexes with pimelate/succinyl-CoA and L-2-aminopimelate with the nonreactive cofactor analog, succinamide-CoA. These structures define the binding conformation of the cofactor succinyl group and its interactions with the enzyme and place its thioester carbonyl carbon in close proximity to the nucleophilic 2-amino group of the acceptor, in support of a direct attack ternary complex mechanism. The acyl group specificity differences between homologous tetrahydrodipicolinate N-acetyl- and N-succinyltransferases can be rationalized with reference to at least three amino acids that interact with or give accessible active site volume to the cofactor succinyl group. These residues account at least in part for the substrate specificity that commits metabolic intermediates to either the succinylase or acetylase branches of the meso-diaminopimelate/lysine biosynthetic pathway.

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Section: Methodsmentioning

confidence: 99%

Acyl group specificity at the active site of tetrahydridipicolinate N‐succinyltransferase

et al. 2002

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“…The corresponding correlation of these excited states is given in Figure 2. Solvents used were chloroform-acetic acid for (2,2), water-DMF for (2,3), and acetic acid for the rest of the molecules [12].…”

Section: Resultsmentioning

confidence: 99%

Molecular Orbital Theory of the Electronic Structure of Organic Compounds IV. A CNDO/S-CI SCF MO Study on the Lower Electronic States of Large Molecules. Singlet-triplet Transitions of Dioxodiazacycloalkanes

Grinberg

Marañon

Sorarrain

1982

Zeitschrift Für Naturforschung A

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The semiempirical molecular orbital CNDO/S-CI spectral parameterization has been used to elucidate the lower triplet electronic states of a series of dioxodiazacycloalkanes. The l 3 B2(no-T*) and l 3 A2 (no-T*) triplet spectroscopic states involve intramolecular charge transfer from the oxygen to the carbon atom of the carbonyl group, which is supported by electron density calculations of these excited states. The solvation energy was incorporated in the calculations.

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“…As can be observed in the corresponding electronic density tables the CNDO/2 method gives the polarizations in good agreement with the electronegativities of the atoms. In particular, the electronic densities of the nitrogen atoms (polarized in the N -H + sense) are linearly related with the chemical shifts of the protons linked to them 1 . The equation (found by the minimum squares method) is (see Fig.…”

Section: Resultsmentioning

confidence: 99%

“…In a previous report 1 we described the generation and spectroscopic properties of the heterocyclic compounds derived from the condensation of succinic and glutaric anhydrides with aliphatic diamines. The principal aim of this paper is to use the semiempirical CNDO/2 and INDO methods for a critical study of the changes in the electronic structure of a dioxodiazacycloalkane caused by the introduction of CH2 groups at either side of the molecule 1 a.…”

Section: Introductionmentioning

confidence: 99%

Molecular Orbital Theory of the Electronic Structure of Organic Compounds

Grinberg

Nudelman

Marañon

et al. 1981

Zeitschrift Für Naturforschung A

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The semiempirical molecular orbital CNDO/S-CI spectral parameterization has been used to elucidate the lower electronic states of a series of dioxodiazacycloalkanes. The a1, b1, and a' occupied molecular orbitals lie predominantly on the oxygen, while a2, b2, and a" are largerly nonbonding orbitals delocalized on the nitrogen and oxygen atoms. The two lowest unoccupied virtual orbitals are predicted to be of b2, a2, and a" symmetry. These orbitals are strongly localized on the C = 0 group. The resulting 1 B2(u0π*) and 1 A2(n0π*) spectroscopic states involve intramolecular charge transfer from the oxygen to the carbon atom of the carbonyl group, which is supported by electron density calculations of these excited states. Although the calculated transition energies may not allow for absolute comparisons with experimental values, it appears that the introduction of self-consistency together with solvation energy and configuration interaction, when the elements of the interaction matrix are properly evaluated, lead to a fairly good interpretation of the singlet-singlet transitions. The lowest energy singlet excited state calculated for each structure is comprised almost entirely of the nπ* configuration.

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Heterocycles derived from the condensation of aliphatic diamines with succinic and glutaric acid derivatives

Cited by 12 publications

References 3 publications

Acyl group specificity at the active site of tetrahydridipicolinate N‐succinyltransferase

Acyl group specificity at the active site of tetrahydridipicolinate N‐succinyltransferase

Molecular Orbital Theory of the Electronic Structure of Organic Compounds IV. A CNDO/S-CI SCF MO Study on the Lower Electronic States of Large Molecules. Singlet-triplet Transitions of Dioxodiazacycloalkanes

Molecular Orbital Theory of the Electronic Structure of Organic Compounds

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