Branched-chain sugar nucleosides. II. 9-(3-Deoxy-3-C-hydroxymethyl-β-D-glucopyranosyl)-adenine

1969 ◽  
Vol 47 (17) ◽  
pp. 3263-3266 ◽  
Author(s):  
Alex Rosenthal ◽  
M. Sprinzl ◽  
H. J. Koch
Keyword(s):  
Sodium Methoxide ◽  
Branched Chain

Application of the oxo reaction to 1,2,4,6-tetra-O-acetyl-3-deoxy-α-D-erythro-hex-2-enopyranose (1), followed by acetylation of the oxo products, gave crystalline 1,2,3′,4,6-penta-O-acetyl-3-deoxy-3-C-(hydroxymethyl)-α-D-glucopyranose (2) in about 30% yield. Conversion of 2 into the branched-chain sugar bromide, followed by condensation of the latter with 6-benzamidochloromercuripurine afforded a blocked branched-chain sugar nucleoside (5) in 67% yield based on 2. The nucleoside (5) was deblocked with methanolic sodium methoxide to afford 9-(3-deoxy-3-C-hydroxymethyl-β-D-glucopyranosyl)-adenine (6) in 75% yield.

Branched-chain sugar nucleosides. IV. 9-(3-Deoxy-3-C-"hydroxymethyl"-β(and α)-D-allofuranosyl and ribofuranosyl)adenine

1969 ◽  
Vol 47 (23) ◽  
pp. 4477-4481 ◽  
Author(s):  
Alex Rosenthal ◽  
Matej Sprinzl
Keyword(s):  
Hydrogen Peroxide ◽  
Sodium Methoxide ◽  
Titanium Tetrachloride ◽  
Total Yield ◽  
Borohydride Reduction ◽  
Peroxide Oxidation ◽  
Alkaline Hydrogen Peroxide ◽  
Sodium Metaperiodate ◽  
Sodium Borohydride Reduction ◽  
Branched Chain

Hydroboration followed by alkaline hydrogen peroxide oxidation of 1,2:5,6-di-O-isopropylidene-3-C-methylene-α-D-ribo-hexofuranose (2) yielded 3-deoxy-3-C-"hydroxymethyl"-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (3) and partially hydrolyzed 3 in a total yield of 88%. Compound 3 was hydrolyzed selectively to the 1,2-monoisopropylidene derivative 5, which was converted via benzoylation followed by acetolysis into the 1,2-diacetate 7. Condensation of the latter compound with chloromercuri-N-benzoyladenine in the presence of titanium tetrachloride, followed by deblocking with methanolic sodium methoxide, yielded 9-(3-deoxy-3-C-"hydroxymethyl"-β(and α)-D-allofuranosyl)adenine in yields of 44 and 4% respectively, based on 7. The over-all yield of 10 based on 3 is 20%. Sodium metaperiodate oxidation of 10, followed by sodium borohydride reduction of the aldehydo-derivative, afforded 9-(3-deoxy-3-C-"hydroxymethyl"-β-D-ribofuranosyl)adenine (11) in 81% yield.Direct acetolysis of 3, followed by conversion of the mixture of peracetates into a mixture of glycosyl chlorides, and finally condensation of the latter with 8 gave the blocked crystalline β-D-nucleoside 9 in an over-all yield of about 9%, based on 3. Subsequent unblocking of 9 gave a nucleoside having the same physical constants as 10.

Branched-chain aminodeoxy sugars. Methyl 3-C-aminomethyl-2-deoxy-α-D-ribo-hexopyranoside and methyl 3-C-aminomethyl-2-deoxy-α-D-arabino hexopyranoside

1970 ◽  
Vol 48 (19) ◽  
pp. 3034-3038 ◽  
Author(s):  
Alex Rosenthal ◽  
Khong-Seng Ong
Keyword(s):  
Catalytic Hydrogenation ◽  
Sodium Methoxide ◽  
Acetyl Derivative ◽  
Molar Equivalent ◽  
Branched Chain

Addition of methyl 4,6-O-benzylidene-2-deoxy-α-D-erythro-hexopyranosid-3-ulose (1) to excess nitromethane and 1 molar equivalent of sodium methoxide in methanol gave methyl 4,6-O-benzylidene-2-deoxy-3-C-nitromethyl-α-D-ribo-hexopyranoside (2) and the arabino stereoisomer 3 in 63 and 22% yields, respectively. The proof of structure of the branched-chain deoxy nitro sugars is described. Debenzylidenation of the nitro sugars afforded the partially blocked nitro sugars 4 and 5. Catalytic hydrogenation of the latter or of 2 and 3 yielded the branched-chain aminodeoxy sugars 7 and 9 (7 characterized as its N-acetyl derivative and 9 as its N-2,4-dinitrophenyl derivative).

Immunocytochemical localization of desmin and vimentin in chick embryonic myocardial cells

1990 ◽  
Vol 48 (3) ◽  
pp. 448-449
Author(s):  
Yukiko Sugi
Keyword(s):  
Sodium Methoxide ◽  
Intermediate Filament Protein ◽  
Chick Embryos ◽  
Immunocytochemical Localization ◽  
Myocardial Cells ◽  
Immunofluorescence Study ◽  
Immunofluorescent Localization ◽  
Rabbit Igg ◽  
Semithin Sections ◽  
Filament Protein

In cultured skeletal muscle cells of chick, one intermediate filament protein, vimentin, is primarily formed and then synthesis of desmin follows. Coexistence of vimentin and desmin has been immunocytochemically confirmed in chick embryonic skeletal musclecells. Immunofluorescent localization of vimentin and desmin has been described in developing myocardial cells of hamster. However, initial localization of desmin and vimentin in early embryonic heart has not been reported in detail. By quick-freeze deep-etch method a loose network of intermediate filaments was revealed to exist surrounding myofibrils. In this report, immunocytochemical localization of desmin and vimentin is visualized in early stages of chick embryonic my ocardium.Chick embryos, Hamburger-Hamilton (H-H) stage 8 to hatch, and 1 day old postnatal chicks were used in this study. For immunofluorescence study, each embryo was fixed with 4% paraformaldehyde and embedded in Epon 812. De-epoxinized with sodium methoxide, semithin sections were stained with primary antibodies (rabbit anti-desmin antibody and anti-vimentin antibody)and secondary antibody (RITC conjugated goat-anti rabbit IgG).

The Weight Loss Effects of Branched Chain Amino Acids and Vitamin B6: A Randomized Controlled Trial on Obese and Overweight Women

2018 ◽  
Vol 88 (1-2) ◽  
pp. 80-89 ◽  
Author(s):  
Zahra Shakibay Novin ◽  
Saeed Ghavamzadeh ◽  
Alireza Mehdizadeh
Keyword(s):  
Amino Acids ◽  
Weight Loss ◽  
Body Composition ◽  
Vitamin B6 ◽  
Controlled Trial ◽  
Density Lipoprotein ◽  
Branched Chain Amino Acids ◽  
Model Assessment ◽  
Waist To Hip Ratio ◽  
Branched Chain

Abstract. Branched chain amino acids (BCAA), with vitamin B6 have been reported to improve fat metabolism and muscle synthesis. We hypothesized that supplementation with BCAA and vitamin B6 would result in more weight loss and improve body composition and blood markers related to cardiovascular diseases. Our aim was to determine whether the mentioned supplementation would affect weight loss, body composition, and cardiovascular risk factors during weight loss intervention. To this end, we performed a placebo-controlled randomized clinical trial in 42 overweight and obese women (BMI = 25–34.9 kg/m2). Taking a four-week moderate deficit calorie diet (–500 kcal/day), participants were randomized to receive BCAA (6 g/day) with vitamin B6 (40 mg/day) or placebo. Body composition variables measured with the use of bioelectrical impedance analysis, homeostatic model assessment, and plasma insulin, Low density lipoprotein, High density lipoprotein, Total Cholesterol, Triglyceride, and fasting blood sugar were measured. The result indicated that, weight loss was not significantly affected by BCAA and vitamin B6 supplementation (–2.43 ± 1.02 kg) or placebo (–1.64 ± 1.48 kg). However, significant time × treatment interactions in waist to hip ratio (P = 0.005), left leg lean (P = 0.004) and right leg lean (P = 0.023) were observed. Overall, supplementation with BCAA and vitamin B6 could preserve legs lean and also attenuated waist to hip ratio.

Branched chain amino acids decrease top-down event-related potentials in healthy subjects

2007 ◽  
Vol 40 (05) ◽  
Author(s):  
AH Neuhaus ◽  
TE Goldberg ◽  
Y Hassoun ◽  
JA Bates ◽  
KW Nassauer ◽  
...  
Keyword(s):  
Amino Acids ◽  
Healthy Subjects ◽  
Event Related Potentials ◽  
Branched Chain Amino Acids ◽  
Top Down ◽  
Related Potentials ◽  
Branched Chain

1576-P: Correlation Analysis between Insulin Sensitivity, Branched-Chain Acid, and Adiponectin Levels in Japanese Individuals with Varying Degrees of Glucose Tolerance

Diabetes ◽  
2020 ◽  
Vol 69 (Supplement 1) ◽  
pp. 1576-P
Author(s):  
ERI AMANO ◽  
KUMIKO YOSHIMURA ◽  
SHOGO FUNAKOSHI ◽  
SEIKI HIRANO ◽  
SATOKO OHMI ◽  
...  
Keyword(s):  
Insulin Sensitivity ◽  
Correlation Analysis ◽  
Glucose Tolerance ◽  
Branched Chain
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