ChemInform Abstract: BRANCHED-CHAIN SUGARS. REACTION OF 1,2-5,6-DI-O-ISOPROPYLIDENE-α-D-RIBO-HEXOFURANOS-3-ULOSE WITH SODIUM CYANIDE AND METHYL NITROACETATE

1976 ◽  
Vol 7 (27) ◽  
pp. no-no
Author(s):  
ALEX ROSENTHAL ◽  
B. L. CLIFF
Keyword(s):  
Sodium Cyanide ◽  
Methyl Nitroacetate ◽  
Branched Chain

Branched-chain sugars. Reaction of 1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose with sodium cyanide and methyl nitroacetate

1976 ◽  
Vol 54 (4) ◽  
pp. 543-547 ◽  
Author(s):  
Alex Rosenthal ◽  
B. L. Cliff
Keyword(s):  
Acetic Anhydride ◽  
Sodium Cyanide ◽  
Equimolar Amount ◽  
Anhydrous Ethanol ◽  
Toluenesulfonic Acid ◽  
Methyl Nitroacetate ◽  
Branched Chain ◽  
Acetate Derivative

Treatment of 1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose (1) with sodium cyanide in anhydrous ethanol followed by addition of an equimolar amount of methyl nitro-acetate gave 3-C-cyano-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (2) in 57% yield. When methyl nitroacetate was first added to sodium cyanide in alcohol followed by the addition of ketose 1 then the allo-cyanohydrin epimer 4 was produced in 85% yield. 3-C-(Carbomethoxy-R,S-nitromethyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (6) was produced in low yield in the latter reaction and was isolated and characterized as its 3-O-acetate derivative 7. Selective acetolysis of the 5,6-O-isopropylidene group of the branched-chain sugars was achieved using acetic anhydride and p-toluenesulfonic acid monohydrate. The proof of structure of the cyano-hydrins is described.

Reactions of nitro sugars. IX. The synthesis of branched-chain dinitro sugars by Michael addition

1968 ◽  
Vol 46 (15) ◽  
pp. 2511-2517 ◽  
Author(s):  
Hans H. Baer ◽  
K. S. Ong
Keyword(s):  
Michael Addition ◽  
Diethyl Malonate ◽  
Side Chain ◽  
Methyl Nitroacetate ◽  
Branched Chain ◽  
Sugar Derivatives ◽  
Asymmetric Carbon

The reaction of methyl 2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-nitro-β-D-glucopyranoside (1) or of methyl 4,6-O-benzylidene-2,3-dideoxy-3-nitro-β-D-erythro-hex-2-enopyranoside (2) with nitroalkanes led to branched-chain dinitro sugar derivatives, namely methyl 4,6-O-benzylidene-2,3-dideoxy-3-nitro-2-nitroalkyl-β-D-glucopyranosides (3). The nitroalkanes employed included nitromethane, nitroethane, 1-and 2-nitropropane, and methyl nitroacetate. The three first-mentioned nitroalkanes were added in similar fashion to methyl 4,6-O-benzylidene-2,3-dideoxy-3-nitro-β-D-threo hex-2-enopyranoside (5) to give methyl 4,6-O-benzylidene-2,3-dideoxy-3-nitro-2-nitroalkyl-β-D-galactopyranosides (6). Analogous reactions of 1 and 5 with diethyl malonate produced the corresponding branched-chain glycosides 7 and 8. The reactions appear to be highly stereoselective as far as the configurations at C-2 and C-3 in the products are concerned. However, there is evidence for the formation of side-chain epimers in three cases where the nitroalkyl side chain possesses an asymmetric carbon.

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

Value of quantitative and qualitative assessment of protein in workers’ diet

2019 ◽  
pp. 97-103
Author(s):  
S. E. Dubenko ◽  
T. V. Mazhaeva ◽  
G. M. Nasybullina
Keyword(s):  
Amino Acids ◽  
Physical Exertion ◽  
Qualitative Evaluation ◽  
Essential Amino Acids ◽  
Qualitative Assessment ◽  
Health State ◽  
Occupational Hazards ◽  
Occupational Groups ◽  
Branched Chain ◽  
Amino Acid Contents

Th e authors reviewed literature on methodic evaluations of human requirements of protein, based on Russian and foreign data bases (Scopus, Web of Science, MedLine, RINTs, eLIBRA RY) via key words in article headings, and evaluated quality and quantity of protein in diets of workers exposed to occupational hazards. Average requirements of amino acids and their additional intake for bett er health state in certain occupational groups remains a topical problem. Th e article covers list of methods for quantitative and qualitative evaluation of proteins in foods and diets. Findings are diff erences in approaches to protein quantity regulation in Russian Federation and WHO/FAO/UNU (protein normal level in RF is higher, depends on physical exertion, with lower quantity of amino acids with branched chain in structure of essential amino acids). Th erapeutic and prophylactic diet corresponding to Order N46 of Russian Health Ministry for main occupations of metallurgic workshops can be considered as high-proteous and balanced in amino acid contents. Necessity is to study adequate intake of amino acids in workers exposed to occupational hazards, for improving protective and adaptative body mechanisms, and prevention of occupational and occupationally conditioned diseases.

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