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PubMed2000

Construction of an enantiomerically pure 6-substituted 3,5-syn-dihydroxyhexanoic acid system by an enantioselective deprotonation strategy: formal synthesis of an antiobesity agent, (-)-tetrahydrolipstatin.

Preparation of 6-substituted 4-hydroxytetrahydro-2H-pyran-2-one (12), a key intermediate for the synthesis of (-)-tetrahydrolipstatin, was achieved in an optically pure form by employing an enantioselective deprotonation reaction of the prochiral bicyclic derivative (5) as a key step.

Anti-Obesity Agents↗
PubMed2005

Solvolysis of (4,5)-anti-4-aryl-5-tosyloxy-2(E)-hexenoate derivatives.

The solvolysis reaction of (4,5)-anti-4-aryl-5-tosyloxy-2(E)-hexenoates 4a-k gave (4,5)-anti-4-aryl-5-hydroxy-2(E)-hexenoates 2a-k and (4,5)-anti-5-aryl-4-hydroxy-2(E)-hexenoates 5a-k along with the complete inversion. This 1,2-aryl migration was induced by treatment with heating in water-saturated nitromethane. On the basis of the substituent effect on the aromatic ring, this 1,2-aryl migration is thought to proceed via the sigma-bridged phenonium ion. The product selectivity between 2a-k and 5a-k was found to be subtly governed by the substituent and substitution pattern in the aromatic ring of the substrates 4a-k.

Caproates↗
PubMed2004

Glycine-arginine-alpha-ketoisocaproic acid improves performance of repeated cycling sprints.

PURPOSE: The purpose of this study was to determine the effect of glycine-arginine-alpha-ketoisocaproic acid (GAKIC) supplementation on repeated bouts of anaerobic cycling performance. METHODS: Ten men completed a randomized, double-blinded, placebo-controlled exercise protocol of two sessions separated by 7 d. Plasma lactate was analyzed in blood collected 45 min before exercise (REST) and 5 min postexercise (POST). Subjects consumed either 11.2-g GAKIC or placebo (PLC) during a 45-min period between the REST and exercise. Mean power, peak power, and fatigue values were assessed from five supramaximal, 10-s cycle ergometer sprints, separated by 1-min rest intervals. Data were analyzed using repeated measures ANCOVA. RESULTS: A significant treatment x time interaction (P = 0.039) was observed for the change in mean power output over the five sprints between the GAKIC and PLC treatments. Post hoc analyses revealed a greater retention of mean power (P = 0.038) between sprints 1 and 2 after GAKIC (-1 +/- 9 W) versus PLC treatment (-47 +/- 18 W). No other performance variables differed between PLC and GAKIC. POST lactate was increased (P < 0.001) above REST, but there was no difference between treatments (P = 0.936). CONCLUSION: These data support an ergogenic effect of GAKIC for attenuating the decline in mean power during repeated bouts of supramaximal exercise.

Adult↗
PubMed1993

Sequencing analysis of mutation points in the biotin operon of biotin-overproducing Escherichia coli mutants.

We analyzed mutation points of the biotin operon from biotin-overproducing mutants of Escherichia coli resistant to two biotin analogs, actithiazic acid and 5-(2-thienyl)-valeric acid, by DNA sequencing. The biotin operons cloned from these mutants were classified into three groups. One point mutation, which was a GC-->AT change within the operator overlapping the -10 region of the rightward (bioB) promoter, was considered to result in disruption of operator structure and enhancement of promoter activity. Two other point mutations, which were both GC-->AT changes just before and after the initiation codon of the bioB gene, were considered to activate the translation efficiency. These mutations significantly accelerated the biotin-forming activity from dethiobiotin in cell-free extracts.

Base Sequence↗
PubMed1996

Design and synthesis of gentiohexaosyl derivatives for an ANP receptor antagonist, HS-142-1.

A hexaosyl fragment of the major component of lipooligosaccharide HS-142-1, O-(3-O-caproyl-beta-D-glucopyranosyl)-(1-->6)-[O-(beta-D- glucopyranosyl)-(1-->6)-O-(3-O-caproyl-beta-D-glucopyranosyl)-(1--> 6)]2-D-glucopyranose (1), was efficiently synthesized by block synthesis. More stable analogs, O-(3-O-hexyl-beta-D-glucopyranosyl)-(1-->6)-[O-(beta-D-glucopyranosyl)- (1-->6)-O-(3-O-hexyl-beta-D-glucopyranosyl)-(1-->6)]2-D-glucopyranose (4) and O-(3-O-caproyl-2,4,6-tri-O-methyl-beta-D-glucopyranosyl)-(1-->6)-[O- (2,3,4-tri-O-methyl-beta-D-glucopyranosyl)-(1-->6)-O-(3-O-caproyl-2,4-di -O- methyl-beta-D-glucopyranosyl)-(1-->6)]2-2,3,4-tri-O-methyl-D-glucopyrano se (2), were also designed and synthesized in a similar manner.

Caproates↗
PubMed2003

Biogenesis of volatile methyl esters in snake fruit (Salacca edulis, Reinw) cv. Pondoh.

The methyl esters of carboxylic acids are characteristic olfactory volatile compounds for the sweet aroma of snake fruit, (Salacca edulis, Reinw) cv. Pondoh. Although methanol was not detected as a volatile constituent, the crude enzymes showed activity to synthesize the methyl esters in the presence of acyl-CoA and methanol. Therefore, the biosynthetic origin of methanol was investigated, resulting in the detection of pectin methyl transferase activity in the flesh. This pectin methyl transferase activity increased during fruit maturation, in parallel with the level of methanol originating from hand-squeezed juice and with the methyl esters extracted from flesh of the fruit. Based on these results, the origin of methanol was confirmed to be the methyl esters of pectins. The crude enzyme also catalyzed the formation of methyl hexanoate, one of the esters of the fruit, in the presence of methyl pectins and hexanoyl-CoA that were used as precursors for a model reaction.

Acyl Coenzyme A↗
PubMed2003

Release characteristics of flavor from spray-dried powder in boiling water and during rice cooking.

The release characteristics of flavor in boiling water and the flavor retention in the rice after cooking were investigated by using spray dried powder in encapsulated in or emulsified with d-limonene or ethyl n-hexanoate in cyclodextrin and maltodextrin, or in gum arabic and maltodextrin. The behavior of flavor release into the boiling water was well simulated by Avrami's equation. The retention of d-limonene and ethyl n-hexanoate in cooked rice was correlated in each case with the flavor amount of spray-dried powder added.

Caproates↗
PubMed1994

Pharmacokinetic determinants of embryotoxicity in rats associated with organic acids.

We have studied four organic acids of similar structure to further understand the basis of their developmental toxicity. Valproic acid (2-propyl pentanoic acid), ethylhexanoic acid, and octanoic acid are isomeric C8 organic acids but their teratologic potency varied widely. Valproic acid induced a moderate to severe teratologic outcome after a single oral administration of 6.25 mmoles/kg on day 12 of rat pregnancy. Twice as much ethylhexanoic acid (12.5 mmoles/kg) induced a less severe response. Octanoic acid was nonteratogenic even at the very high dose of 18.75 mmoles/kg. This latter result is undoubtedly due to poor intestinal absorption of octanoic acid, as the maternal plasma levels never reached half of those measured for valproic acid and ethylhexanoic acid. Moreover, only a tiny fraction of that in maternal plasma was actually transferred into the embryo. On the other hand, the peak concentration and duration of exposure to valproic acid and ethylhexanoic acid were very similar despite a more severe teratologic outcome following valproic acid, which indicated higher intrinsic activity of this latter agent. A fourth agent, methylhexanoic acid, was also studied and had no teratogenic effects when given at 14.1 mmoles/kg. Pharmacokinetic studies of this agent revealed higher peak concentrations in maternal plasma and embryo than valproic acid or ethylhexanoic acid, but the duration of exposure was shorter. We conclude that pharmacokinetic parameters can be important determinants of teratologic outcome and thereby help explain differing potencies of structurally similar chemicals.

Abnormalities, Drug-Induced↗
PubMed2005

Simultaneous biocatalyst production and Baeyer-Villiger oxidation for bioconversion of cyclohexanone by recombinant Escherichia coli expressing cyclohexanone monooxygenase.

Cyclohexanone monooxygenase (CHMO) catalyzing Baeyer-Villiger oxidation converts cyclic ketones into optically pure lactones, which have been used as building blocks in organic synthesis. A recombinant Escherichia coli BL21(DE3)/pMM4 expressing CHMO originated from Acinetobacter sp. NCIB 9871 was used to produce epsilon-caprolactone through a simultaneous biocatalyst production and Baeyer-Villiger oxidation (SPO) process. A fed-batch process was designed to obtain high cell density for improving production of epsilon-caprolactone. The fed-batch SPO process gave the best results, 10.2 g/L of epsilon-caprolactone and 0.34 g/(L.h) of productivity, corresponding to a 10.5- and 3.4-fold enhancement compared with those of the batch SPO, respectively.

Acinetobacter↗
PubMed2006

Production of natural fruity aroma by Geotrichum candidum.

Based on its aromatic potential, Geotrichum candidum isolated from olive vegetation water was tested for the production of volatile compounds. When G. candidum was cultivated on media with glucose as the carbon source, flavor volatile compounds were produced and accumulated in the broth. Fruity flavoring compounds (pineapple-like) such as esters and alcohols were analyzed by gas chromatography coupled to mass spectrometry, including ethyl esters of acetic acid and butyric acid, methyl-3-butan-1-ol, and methyl-2-propan-1-ol. Their synthesis corresponded to the stationary growth phase of the strain. Production of the volatile compounds reached 9.5 g/L of 2-hexanoic acid ethyl ester and 1.6 g/L of benzaldehyde as the main concentrated molecules. Ethyl alcohol seems to be an intermediate metabolite in this pathway.

Acetates↗
PubMed1987

Inhibitory effect of progesterone in the postcastration gonadotrophin rise in women.

This study was designed to investigate the effects of progesterone on the gonadotrophin rise after bilateral salpingo-oophorectomy (BSO). Twenty-eight regularly menstruating women underwent hysterectomy and BSO during the follicular phase of the menstrual cycle. They were divided into 5 groups depending on the treatment after BSO. Plasma LH and FSH were studied serially for 14 days after BSO and the patterns of LH and FSH rises were contrasted to those observed in the control group which received neither progesterone nor estrogen. LH and FSH levels in the group which were given low dose progesterone only, rose consistently after BSO and these patterns were similar to those seen in the control group. However, the addition of estrogen reduced gonadotrophin rises significantly more than estrogen did alone. Further, the luteal phase level of progesterone solely has a suppressive effect on the gonadotrophin rises after BSO. Our observations suggest that synergism of progesterone with estrogen may exist in suppressing gonadotrophin secretion in the normal luteal phase and should help in understanding why gonadotrophin levels in the luteal phase are lower than those in the follicular phase of the menstrual cycle.

17 alpha-Hydroxyprogesterone Caproate↗
PubMed1990

Cholesterol side-chain cleavage activity in the human umbilical cord in vitro.

With a view to establish whether cells of the human umbilical cord possess cholesterol side-chain cleavage activity, homogenates of term umbilical cord obtained following spontaneous vaginal delivery from uncomplicated pregnancies (n = 6; 38-40 weeks gestation) were incubated with 26-14C cholesterol. Controls were homogenates heating in a boiling water bath for 10 min. Proof of the existence of cholesterol C-20, 22-desmolase activity in the viable tissue was established by associating radioactivity due to the labelled carbon 26 of 26-14C cholesterol with the p-bromophenacyl ester of isocaproic acid by reverse-isotope dilution analysis. The desmolase efficiency expressed as specific activity of 14C isocaproic acid, dpm g-1 tissue varied from 110 to 351 with a mean of 202. The small but definite conversion indicates that the cholesterol side-chain cleavage reaction previously believed to be exclusive to the steroidogenic pathway operating in the adrenal, gonads and placenta does exist in the human term umbilical cord in vitro.

Adult↗