Synthesis and crystal structure of pyrroloquinoline quinol (PQQH2) and pyrroloquinoline quinone (PQQ)

2017 ◽  
Vol 73 (3) ◽  
pp. 489-497 ◽  
Author(s):  
Kazuto Ikemoto ◽  
Shigeki Mori ◽  
Kazuo Mukai
Keyword(s):  
Crystal Structure ◽  
Vitamin C ◽  
Mixed Solvent ◽  
Pyrroloquinoline Quinone ◽  
Crystal Structure Analysis ◽  
Disodium Salt ◽  
Water Soluble ◽  
High Yield ◽  
Synthesis And Crystal Structure ◽  
First Time

Pyrroloquinoline quinone (PQQ) is a water-soluble quinone compound first identified as a cofactor of alcohol- and glucose-dehydrogenases (ADH and GDH) in bacteria. For example, in the process of ADH reaction, alcohol is oxidized to the corresponding aldehyde, and inversely PQQ is reduced to pyrroloquinoline quinol (PQQH2). PQQ and PQQH2molecules play an important role as a cofactor in ADH and GDH reactions. However, crystal structure analysis has not been performed for PQQ and PQQH2. In the present study, the synthesis of PQQH2powder crystals was performed under air, by utilizing vitamin C as a reducing agent. By reacting a trihydrate of disodium salt of PQQ (PQQNa2·3H2O) with excess vitamin C in H2O at 293 and 343 K, yellowish brown and black powder crystals of PQQH2having different properties were obtained in high yield, respectively. The former was PQQH2trihydrate (PQQH2·3H2O) and the latter was PQQH2anhydrate (PQQH2). Furthermore, sodium-free red PQQ powder crystal (a monohydrate of PQQ, PQQ·H2O) was prepared by the reaction of PQQNa2·3H2O with HCl in H2O. Single crystals of PQQH2and PQQ were prepared from Me2SO/CH3CN mixed solvent, and we have succeeded in the crystal structure analyses of PQQH2and PQQ for the first time.

Bis(triphenylphosphine)gold(I) Perrhenate

2013 ◽  
Vol 68 (11) ◽  
pp. 1173-1179 ◽  
Author(s):  
Sebastian A. Baer ◽  
Alexander Pöthig ◽  
Salem M. Bawaked ◽  
Hubert Schmidbaur ◽  
Florian Kraus
Keyword(s):  
Crystal Structure ◽  
Mixed Solvent ◽  
High Yield ◽  
Nmr Data ◽  
Π Stacking ◽  
Interionic Interactions ◽  
P Ligands

Bis(triphenylphosphine)gold(I) perrhenate [Ph3PAuPPh3]+ReO4 - has been prepared in high yield from Ph3PAuCl, Ph3P and AgReO4 in a mixed solvent. The compound is stable in air and decomposes at 235 °C. In the crystal structure, the two independent perrhenate anions are not approaching the gold centers of the two independent cations, but weak interionic interactions are entertained via π-π stacking of phenyl groups and C-H···O contacts. As three-blade chiral rotors, the Ph3P ligands of the cations are in a staggered conformation at the gold atoms with only slightly bent P-Au-P axes. IR and NMR data show no anomalies and are close to those of alkali or onium perrhenates.

scholarly journals Ultrasonic synthesis and crystal structure analysis of two trimethylsilyloxy-substituted bicyclo[2.2.2]octene derivatives

2013 ◽  
Vol 125 (5) ◽  
pp. 1079-1085 ◽  
Author(s):  
H T SRINIVASA ◽  
H NAGARAJAIAH ◽  
B S PALAKSHAMURTHY ◽  
S HARIPRASAD ◽  
NOOR SHAHINA BEGUM
Keyword(s):  
Crystal Structure ◽  
Structure Analysis ◽  
Crystal Structure Analysis ◽  
Synthesis And Crystal Structure ◽  
Ultrasonic Synthesis

Synthesis and crystal structure analysis of 1,5-disubstituted 9-thiabarbaralane 9,9-dioxides

1977 ◽  
Vol 18 (14) ◽  
pp. 1249-1252 ◽  
Author(s):  
Gary G. Christoph ◽  
Steve Hardwick ◽  
Ulla Jacobsson ◽  
Yun-Bai Koh ◽  
Rudi Moerck ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Structure Analysis ◽  
Crystal Structure Analysis ◽  
Synthesis And Crystal Structure

scholarly journals An ambient stable core-substituted perylene bisimide dianion: isolation and single crystal structure analysis

2015 ◽  
Vol 6 (3) ◽  
pp. 1663-1667 ◽  
Author(s):  
Sabine Seifert ◽  
David Schmidt ◽  
Frank Würthner
Keyword(s):  
Crystal Structure ◽  
Single Crystal ◽  
Structure Analysis ◽  
Crystal Structure Analysis ◽  
Disodium Salt ◽  
Single Crystal Structure ◽  
Perylene Bisimide ◽  
Stable Core ◽  
Single Crystal Structure Analysis

The reduction of a highly electron deficient PBI afforded the corresponding dianion disodium salt that was characterized by single crystal structure analysis.

scholarly journals Molecular mechanism(s) involved in differential expression of vitamin C transporters along the intestinal tract

2017 ◽  
Vol 312 (4) ◽  
pp. G340-G347 ◽  
Author(s):  
Veedamali S. Subramanian ◽  
Padmanabhan Srinivasan ◽  
Alexis J. Wildman ◽  
Jonathan S. Marchant ◽  
Hamid M. Said
Keyword(s):  
Ascorbic Acid ◽  
Vitamin C ◽  
Differential Expression ◽  
Molecular Mechanism ◽  
Mammalian Cells ◽  
Intestinal Tract ◽  
Water Soluble ◽  
Differentially Expressed ◽  
Epigenetic Mechanism ◽  
First Time

Mammalian cells utilize two transporters for the uptake of ascorbic acid (AA), Na+-dependent vitamin C transporter SVCT-1 and SVCT-2. In the intestine, these transporters are involved in AA absorption and are expressed at the apical and basolateral membrane domains of the polarized epithelia, respectively. Little is known about the differential expression of these two transporters along the anterior-posterior axis of the intestinal tract and the molecular mechanism(s) that dictate this pattern of expression. We used mouse and human intestinal cDNAs to address these issues. The results showed a significantly lower rate of carrier-mediated AA uptake by mouse colon than jejunum. This was associated with a significantly lower level of expression of SVCT-1 and SVCT-2 at the protein, mRNA, and heterogeneous nuclear RNA (hnRNA) levels in the colon than the jejunum, implying the involvement of transcriptional mechanism(s). Similarly, expression levels of SVCT-1 and SVCT-2 mRNA and hnRNA were significantly lower in human colon. We also examined the levels of expression of hepatocyte nuclear factor 1α and specificity protein 1, which drive transcription of the Slc23a1 and Slc23a2 promoters, respectively, and found them to be markedly lower in the colon. Furthermore, significantly lower levels of the activating markers for histone (H3) modifications [H3 trimethylation of lysine 4 (H3K4me3) and H3 triacetylation of lysine 9 (H3K9ac)] were observed in the Slc23a1 and Slc23a2 promoters in the colon. These findings show, for the first time, that SVCT-1 and SVCT-2 are differentially expressed along the intestinal tract and that this pattern of expression is, at least in part, mediated via transcriptional/epigenetic mechanisms. NEW & NOTEWORTHY Our findings show, for the first time, that transporters of the water-soluble vitamin ascorbic acid (i.e., the vitamin C transporters SVCT-1 and SVCT-2) are differentially expressed along the length of the intestinal tract and that the pattern of expression is mediated, at least in part, by transcriptional and epigenetic mechanism(s) affecting both Slc23a1 and Slc23a2 genes.

Synthesis and crystal structure analysis of binary molybdate CsNamoO4 · 2H2O

1997 ◽  
Vol 38 (4) ◽  
pp. 615-619 ◽  
Author(s):  
P. V. Klevtsov ◽  
L. A. Glinskaya ◽  
R. F. Klevtsova ◽  
K. S. Aleksandrov
Keyword(s):  
Crystal Structure ◽  
Structure Analysis ◽  
Crystal Structure Analysis ◽  
Synthesis And Crystal Structure
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