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Title: 3-(2-Biphenyl)sydnone

Abstract

The title compound, C{sub 14}H{sub 10}N{sub 2}O{sub 2}, is one of many sydnones which have been synthesized in order to investigate the influence of substituents and sydnone-ring stability. There is medicinal interest in the sydnone if the ring can predictably release NO. Bond lengths and angles of the sydnone ring were compared with those of other published sydnone compounds and were found to fit the average of the published data.

Authors:
; ;  [1]
  1. (WSU)
Publication Date:
Research Org.:
Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS)
Sponsoring Org.:
USDOE
OSTI Identifier:
1008710
Resource Type:
Journal Article
Resource Relation:
Journal Name: Acta Crystallogr. E; Journal Volume: 60; Journal Issue: 2004
Country of Publication:
United States
Language:
ENGLISH
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; KETONES; SYNTHESIS; BOND LENGTHS; STABILITY

Citation Formats

Riddle, Gordon B., Grossie, David A., and Turnbull, Kenneth. 3-(2-Biphenyl)sydnone. United States: N. p., 2010. Web.
Riddle, Gordon B., Grossie, David A., & Turnbull, Kenneth. 3-(2-Biphenyl)sydnone. United States.
Riddle, Gordon B., Grossie, David A., and Turnbull, Kenneth. 2010. "3-(2-Biphenyl)sydnone". United States. doi:.
@article{osti_1008710,
title = {3-(2-Biphenyl)sydnone},
author = {Riddle, Gordon B. and Grossie, David A. and Turnbull, Kenneth},
abstractNote = {The title compound, C{sub 14}H{sub 10}N{sub 2}O{sub 2}, is one of many sydnones which have been synthesized in order to investigate the influence of substituents and sydnone-ring stability. There is medicinal interest in the sydnone if the ring can predictably release NO. Bond lengths and angles of the sydnone ring were compared with those of other published sydnone compounds and were found to fit the average of the published data.},
doi = {},
journal = {Acta Crystallogr. E},
number = 2004,
volume = 60,
place = {United States},
year = 2010,
month =
}
  • The metabolism of /sup 14/C-labeled PCBs (polychlorinated biphenyls), which comprised the Aroclor 1242 mixture, was greatly enhanced by the addition of biphenyl (BP) to soil. After 49 days, only 25 to 35% of the original PCBs remained in the soil, and 48 to 49% was converted to /sup 14/CO/sub 2/ (including soil carbonates) in treatment enriched with BP; by contrast, 92% of the PCBs remained and less than 2% was converted to /sup 14/CO/sub 2/ in the unenriched control. Although the mineralization of PCBs in soils inoculated with Acinetobacter strain P6 was not greater than that in uninoculated BP-enriched soils,more » the initial and maximum mineralization rates and mineralization of BP was consistent with kinetic models based upon linear-no growth and exponential growth; lower cell densities (< 10/sup 6//g) of BP-oxidizing bacteria gave a better fit for exponential growth, whereas the highest cell density (10/sup 9//g) gave a better fit for linear-no growth. The numbers of BP-oxidizing bacteria declined exponentially upon depletion of the substrate. Since the mineralization of the chlorinated cometabolites was brought about by microorganisms (comensals) other than BP oxidizers, /sup 14/CO/sub 2/ production could not be fit to either of the two growth models. However, /sup 14/CO/sub 2/ production from the highest-density inoculum could be fit to a first-order (no-growth) sequential-reaction series.« less
  • The authors cloned the entire bphABCD genes encoding degradation of biphenyl and polychlorinated biphenyls to benzoate and chlorobenzoates from the chromosomal DNA of Pseudomonas putida KF715. The nucleotide sequence revealed two open reading frames corresponding to the bphC gene encoding 2,3-dihydroxybiphenyl dioxygenase and the bphD gene encoding 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid (ring-meta-cleavage compound) hydrolase.
  • Rhodococcus sp. strain RHA1 is a gram-positive polychlorinated biphenyl (PCB) degrader which can degrade 10 ppm of PCB-48 (equivalent to Aroclor 1248), including tri-, tetra-, and pentachlorobiphenyls, in a few days. We isolated the 7.6-kb EcoRI-BamHI fragment carrying the biphenyl catabolic genes of RHA1 and determined their nucleotide sequence. On the basis of deduced amino acid sequence homology, we identified six bph genes, bphA1A2A3A4, bphB, and bphC, that are responsible for the initial three steps of biphenyl degradation. The order of bph genes in RHA1 is bphA1A2A3A4-bphC-bphB. This gene order differs from that of other PCB degraders reported previously. Themore » amino acid sequences deduced from the RHA1 bph genes have a higher degree of homology with the tod genes from Pseudomonas putida F1 (49 to 79%) than with the bph genes of Pseudomonas sp. strains KF707 and KKS102 (30-65%). FIn Escherichia coli, bphA gene activity was not observed even when expression vectors were used. The activities of bphB and bphC, however, were confirmed by observing the transformation of biphenyl to a meta-cleavage compound with the aid of benzene dioxygenase activity that complemented the bphA gene activity (S. Irie, S. Djoi, T. Yorifuji, M. Takagi, and K. Yano, J. Bacteriol. 169:5174-5179, 1987). The expected products of the cloned bph genes, except bphA3, were observed in E. coli in an in vitro transcription-translation system. Insertion mutations of bphA1 and bphC of Rhodococcus sp. strain RHA1 were constructed by gene replacement with cloned gene fragments. The bphA1 and bphC insertion mutants lost the ability to grow on biphenyl, demonstrating that the cloned bph genes are essential for biphenyl catabolism in this strain. 31 refs., 5 figs., 2 tabs.« less
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