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Treatment of 2'-carbonyl-alpha-C-glycopyranosides of gluco, galacto, manno, 2-deoxy, and 2-azido sugars with 4% NaOMe resulted in anomeric epimerization to give their respective beta-anomers in good to excellent yields. The epimerization of the 2'-aldehyde of alpha-C-galactopyranoside (10) in deuterium methanol, which afforded the beta-anomer with exclusive deuterium replacements at the 1'-position, excluded the possibility of the exo-glycal as being involved as an intermediate. When 2'-aldehyde (36) and 2'-ketone (41) of 2,3-di-O-benzyl-alpha/beta-l-C-arabinofuranoside were used as substrates we were able to obtain the respective equatorial alpha-C-arabinopyranosides (37 and 42). These observations confirmed that the epimerization involves an acyclic alpha,beta-unsaturated aldehyde or ketone, which is formed by the enolation of 2'-carbonyl-alpha-C-glycoside with subsequent beta-elimination. Thereafter an intramolecular hetero-Michael cycloaddition occurs, leading to the formation of thermodynamically controlled stable products, which were exclusively the equatorial C-glycopyranosides, except in the case of 2'-carbonyl-C-furanosides, where a mixture of two anomers was obtained.

Aims To study the associations between fat distribution and lung functions in healthy subjects of young adults and to explore potential gender difference in these correlations. Methods A total of 2101 adult participants were recruited. Height, weight, and vital capacity index (VCI) were measured and recorded according to the national physical fitness test standard. Body compositions, including body mass index (BMI), body fat percentage (BFP), waist-to-hip ratio (WHR), fat-free mass (FFM), trunk muscle mass (TMM), fat mass (FM), visceral fat area (VFA), visceral adipose tissue (VAT), and subcutaneous adipose tissue (SAT), were conducted using body composition analyzer. Data were analyzed by SPSS 20.0 software. Results We found that male participants showed significantly higher BMI, WHR, FFM, TMM, VFA, and VCI, but lower FM, BFP, and SAT in comparison with women. However, there was no significant difference in VAT between the male and female. Lung functions represented by VCI were negatively correlated with FM, VAT, SAT, and VFA for both men and women ( r < 0; P < 0.05). Among these negative correlations, VCI was more inversely correlated with VFA for men but with SAT for women, respectively. After dividing the whole populations by BMI, BFP, and WHR, further correlation analysis showed VCI was still more negatively correlated with VFA for all male subgroups ( r < 0; P < 0.05). On the contrary, VCI was more negatively correlated with SAT in BMI-underweight, BMI-normal, BFP-low fat, BFP-normal fat, WHR-normal, and WHR-obese subgroups ( r < 0; P < 0.05), while VFA and VAT was more inversely correlated with VCI in BMI- and BFP-overweight+obese subgroups ( r < 0; P < 0.05). Conclusions Fat accumulation is highly associated with the vital capacity index in young adults. In general, VCI was more negatively correlated with VFA for men but with SAT for women, respectively, in comparison with other tested indices.