Synthesis of 6-chloro-9-(6′-deoxy-3′-C-methyl-2′,3′,4′-tri-O-methyl- β-D-allopyranosyl)purine: a branched-chain sugar nucleoside

1968 ◽  
Vol 46 (23) ◽  
pp. 3691-3694 ◽  
Author(s):  
G. B. Howarth ◽  
W. A. Szarek ◽  
J. K. N. Jones
Keyword(s):  
Acetyl Derivative ◽  
Purine Nucleoside ◽  
Fusion Method ◽  
Pyranose Ring ◽  
Branched Chain

The preparation of 6-deoxy-3-C-methyl-2,3,4-tri-O-metliyl-D-allopyranose (7), a branclied-chain sugar with the same constitution as nogalose from the antibiotic nogalamycin, is described. Condensation of the 1-O-acetyl derivative 8 with 6-chloropurine by the fusion method gave 6-chloro-9-(6′-deoxy-3′-C-methyl-2′,3′,4′-tri-O-methyl-β-D-allopyranosyl)purine (9), which to our knowledge is the first synthetic, purine nucleoside containing a branched-chain sugar with a pyranose ring.

Branched-chain sugar nucleosides. Synthesis of a purine nucleoside of 4-O-acetyl-L-arcanose

1969 ◽  
Vol 34 (2) ◽  
pp. 476-477 ◽  
Author(s):  
G. B. Howarth ◽  
W. A. Szarek ◽  
John K. N. Jones
Keyword(s):  
Purine Nucleoside ◽  
Branched Chain

Photoamidation of 3,4,6-Tri-O-acetyl-1,2-dideoxy-D-arabino-hex-1-enopyranose

1972 ◽  
Vol 50 (8) ◽  
pp. 1192-1198 ◽  
Author(s):  
Alex Rosenthal ◽  
A. Zanlungo
Keyword(s):  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Acetyl Derivative ◽  
Lithium Aluminum ◽  
Hydride Reduction ◽  
Branched Chain

The acetone-initiated photochemical addition of formamide to 3,4,6-tri-O-acetyl-1,2-dideoxy-D-arabino-hex-1-enopyranose (1) afforded 3,4,6-tri-O-acetyl-2,6-anhydro-3-deoxy-D-gluco-heptonamide (2), 3,4,6-tri-O-acetyl-2,6-anhydro-3-deoxy-D-manno-heptonamide (3), and3,4,6-tri-O-acetyl-1,5-anhydro-2-C-carbamoyl-1,2-dideoxy-D-gluco-hexitol (4) in a combined yield of about 75% (the ratio of yields of 2,3, and 4 was approximately 2:2:3). In addition, trace quantities of the epimeric manno branched-chain adduct of 4, and acetone adducts of 1 were formed. Lithium aluminum hydride reduction of 4 yielded a branched-chain aminopolyol, isolated as its N-acetyl derivative.

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).

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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