Journal of Carbohydrate Chemistry最新文献

{"title":"Structural characteristics and biological activity of different alginate blocks extracted from brown seaweed Turbinaria ornata","authors":"Thuy T.T. Thanh ,&nbsp;Thu T.M. Quach ,&nbsp;Van T.T. Tran ,&nbsp;Thanh V. Nguyen ,&nbsp;Shiho Suzuki ,&nbsp;Shinichi Kitamura ,&nbsp;Yoshiaki Yuguchi","doi":"10.1080/07328303.2021.1928155","DOIUrl":"10.1080/07328303.2021.1928155","url":null,"abstract":"<div><p>An alginate (molecular weight [<em>M</em>w] = 64.8 × 10³, <em>F</em>_M = 0.505) was extracted from brown seaweed <em>Turbinaria ornata</em>, and were separated into three fractions, G-blocks (<em>M</em>w = 8.0 × 10³, <em>F</em>_M = 0.141), M-blocks (<em>M</em>w = 4.0 × 10³, <em>F</em>_M = 0.952), and MG-blocks (<em>M</em>w = 8.0 × 10³, <em>F</em>_M = 0.279). According to biological evaluations in terms of antimicrobial, antioxidant, and cytotoxic activities, the native alginate was not a high bioactive compound, but its two main fractions, G-blocks and M-blocks especially M-blocks, showed higher activities. The native alginate and two main fractions were found to have a linear single-chain conformation in saline solution as observed by small-angle X-ray scattering (SAXS) measurements.</p></div><div><h3>Graphical Abstract</h3><p><span><figure><span><img><ol><li><span>Download : <span>Download high-res image (211KB)</span></span></li><li><span>Download : <span>Download full-size image</span></span></li></ol></span></figure></span></p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"40 1","pages":"Pages 97-114"},"PeriodicalIF":1.0,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2021.1928155","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41581895","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Chiral acidic amino acids as tethers for intramolecular glycosylation","authors":"Katsuya Fukushima ,&nbsp;Takashi Kikuma ,&nbsp;Yoichi Takeda","doi":"10.1080/07328303.2021.2015364","DOIUrl":"10.1080/07328303.2021.2015364","url":null,"abstract":"<div><p>Intramolecular glycosylation with peptides as tethers is attractive for the synthesis of oligosaccharides because conjugation between the amino acids present in the tethers is facile. However, few studies have been published about the effects of the amino acid side chain length and amino acid chirality on the glycosylation process. In this study, we revealed that the chain length of the amino acid can regulate the regioselectivity of the glycosylation process based on our observation that the 1,2-linked products were preferred when tethers were those having aspartic acid residues linked to each other, while 1,3-linked products were preferred for glutamic acid-based tethers. However, the amino acid chirality was found to have no effect on the yield and stereoselectivity of the glycosylation reaction.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"40 6","pages":"Pages 283-307"},"PeriodicalIF":1.0,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48890495","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Stereoselective glycosylation with conformation-constrained 2-Nitroglycals as donors and bifunctional thiourea as catalyst","authors":"Yongyong Wan ,&nbsp;Xiaopei Wu ,&nbsp;Yunxia Xue ,&nbsp;Xi-E Lin ,&nbsp;Liming Wang ,&nbsp;Jian-Song Sun ,&nbsp;Qingju Zhang","doi":"10.1080/07328303.2021.2023560","DOIUrl":"10.1080/07328303.2021.2023560","url":null,"abstract":"<div><p>Herein, we report a novel method for highly efficient and stereoselective construction 1,2<em>-cis</em>-2-amino-2-deoxy-glycosidic linkages using conformation-constrained 2-nitroglycal donors and bifunctional thiourea catalyst. The method enjoys mild reaction conditions, good to excellent stereoselectivity, broad substrate scope, and good to excellent efficiency.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"40 7","pages":"Pages 535-557"},"PeriodicalIF":1.0,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44931952","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Chemical synthesis of TMG-chitotriomycin","authors":"Yunqin Zhang ,&nbsp;Guozhi Xiao","doi":"10.1080/07328303.2021.2009504","DOIUrl":"10.1080/07328303.2021.2009504","url":null,"abstract":"<div><p>TMG-chitotriomycin is a recently discovered β-<em>N</em>-acetylglucosaminidase (GlcNAcase) inhibitor, specific for insect and fungal GlcNAcases. Chemical synthesis is a reliable and effective means to solve the attainability issues of TMG-chitotriomycin, which could facilitate in-depth studies of its biological activities. Thus far, four different synthetic routes toward TMG-chitotriomycin have been reported. Herein, we provide a comprehensive review on the chemical synthesis of TMG-chitotriomycin.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"40 7","pages":"Pages 327-338"},"PeriodicalIF":1.0,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47271462","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Immunological studies of Morinda officinalis: How polysaccharides act as adjuvants","authors":"Haibo Feng ,&nbsp;Hui Zhi ,&nbsp;Xin Hu ,&nbsp;Yan Yang ,&nbsp;Linzi Zhang ,&nbsp;Qianqian Liu ,&nbsp;Yangyang Feng ,&nbsp;Daiyan Wu ,&nbsp;Xiaonong Yang","doi":"10.1080/07328303.2021.1954657","DOIUrl":"10.1080/07328303.2021.1954657","url":null,"abstract":"<div><p><em>Morinda officinalis</em> polysaccharides (MOPS) were investigated for their physicochemical properties, monosaccharide composition, and immune-modulating effects <em>in vitro</em> and <em>in vivo</em>. <em>In vitro</em>, MOPS significantly promoted lymphocyte proliferation and increased IFN-γ and IL-4 secretion. <em>In vivo</em>, MOPS acted as adjuvant, which significantly up-regulated HBsAg-specific IgG and IgG isotype levels, promoted antigen-specific T cell proliferation and cytokine (IL-2 and IL-5) production, and induced CTL and NK cytotoxicity. Moreover, MOPS increased DC maturation. Overall, MOPS can serve as an adjuvant to promote humoral and cellular immune responses via promoting DC maturation, suggesting that MOPS may have potentials as a natural immune-enhancing agent.</p><p><span><figure><span><img><ol><li><span>Download : <span>Download high-res image (850KB)</span></span></li><li><span>Download : <span>Download full-size image</span></span></li></ol></span></figure></span></p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"40 4","pages":"Pages 156-178"},"PeriodicalIF":1.0,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2021.1954657","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49437809","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Evaluating the reactivity and stereoselectivity of salicyl-type thioglycosides as non-malodorous thioglycoside alternatives for oligosaccharide synthesis","authors":"Hirofumi Dohi ,&nbsp;Risa Sakurai ,&nbsp;Manami Tamura ,&nbsp;Ryota Komai ,&nbsp;Yoshihiro Nishida","doi":"10.1080/07328303.2021.1921787","DOIUrl":"10.1080/07328303.2021.1921787","url":null,"abstract":"<div><p>Herein, <em>o</em>-(methoxycarbonyl)phenyl thioglycosides [or (methyl)salicyl 1-thioglycosides] were evaluated as non-malodorous thioglycoside alternatives. The <em>o</em>-methoxycarbonyl group was expected to assist in the departure of leaving group. Salicyl-type thioglycosides exhibited high reactivity and glycosylation yields when <em>N</em>-iodosuccinimide and trifluoromethanesulfonic acid were used as promoters. Glycosylation with these thioglycosides in dichloromethane showed similar reactivity and stereoselectivity as those of phenyl thioglycosides. Glycosylation with <em>per</em>-<em>O</em>-benzyl salicyl-type thioglycosides in dichloromethane showed 1,2-<em>cis</em>-selectivity, while the same reaction in nitriles afforded predominantly 1,2-<em>trans</em> glycosides. In contrast, glycosylation with <em>per</em>-<em>O</em>-benzoyl thioglycosides afforded exclusively 1,2-<em>trans</em> glycosides. These results strongly suggest that salicyl-type thioglycosides can serve as non-malodorous alternatives for phenyl thioglycosides.</p></div><div><h3>Graphical Abstract</h3><p><span><figure><span><img><ol><li><span>Download : <span>Download high-res image (190KB)</span></span></li><li><span>Download : <span>Download full-size image</span></span></li></ol></span></figure></span></p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"40 1","pages":"Pages 45-65"},"PeriodicalIF":1.0,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2021.1921787","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49516487","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Purification, structural elucidation and immunostimulatory effect of a new protein-polysaccharide conjugate produced by Nervilia fordii","authors":"Jizhao Xie ,&nbsp;Li Qiu ,&nbsp;Luhui Zou ,&nbsp;Yunfeng Xie ,&nbsp;Di Luo ,&nbsp;Huanji Xu ,&nbsp;Xinduo Wu ,&nbsp;Lisheng Wang","doi":"10.1080/07328303.2021.1975733","DOIUrl":"10.1080/07328303.2021.1975733","url":null,"abstract":"<div><p>A novel protein-polysaccharide conjugate NFP-A4 was isolated and purified from water extracts of <em>Nervilia fordii.</em> The polysaccharide chain of NFP-A4 was found to contain D-galacturonic acid, D-galactose, D-glucose, L-arabinose, D-glucuronic acid, L-rhamnose, and D-mannose. The protein content of NFP-A4 was determined to be 12.83%, and it was bound to the polysaccharide chain via <em>O</em>-linkages at the serine and threonine residues. NFP-A4 was found to significantly activate macrophages and also induce immunomodulatory responses. These data suggest that NFP-A4 is a major bioactive component of <em>N. fordii</em> and may be responsible for many of its therapeutic properties.</p><p><span><figure><span><img><ol><li><span>Download : <span>Download high-res image (370KB)</span></span></li><li><span>Download : <span>Download full-size image</span></span></li></ol></span></figure></span></p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"40 5","pages":"Pages 226-242"},"PeriodicalIF":1.0,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44097282","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Large-Scale Beard Extraction Enhances the Cosmetic Results of Scalp Hair Restoration in Advanced Androgenetic Alopecia in East Asian Men: A Retrospective Study.","authors":"De-Cong Zhu, Ye He, Zhe-Xiang Fan, Jin Wang, Qian Qu, Zhi-Qi Hu, Yong Miao","doi":"10.1007/s13555-019-00344-z","DOIUrl":"10.1007/s13555-019-00344-z","url":null,"abstract":"<p><strong>Introduction: </strong>Beard hair serves as an important additional donor supply to support hair transplantation in hirsute patients with extensive alopecia and lacking sufficient occipital hair. However, the efficacy and safety of large-scale beard hair extraction have not been studied extensively in the East Asian population.</p><p><strong>Methods: </strong>Data obtained from hirsute patients with extensive alopecia who underwent hair transplantation between March 2017 and December 2018 at Nanfang Hospital were analyzed. Occipital and beard hair were evaluated separately during the pre-, intra-, and post-operative periods. Individual beard hair follicular units (FUs) were harvested under tumescence using a hollow punch with an outer diameter of 0.8-0.9 mm. Follow-up examinations were scheduled at 3-5 days, 1 month, and 9 months postoperatively to check for complications, determine the survival rate of mixed, transplanted FU grafts, and assess patient satisfaction. Data were collected and analyzed statistically.</p><p><strong>Results: </strong>A total of 36 hirsute, male patients with advanced androgenetic alopecia (AGA) (Norwood-Hamilton V-VI) were included in this study. The density of the occipital and beard areas was 78.6 ± 4.6 and 48.4 ± 9.3 FU, respectively. It took 3.1 ± 0.9 h to harvest 3135 ± 863 FUs from the occipital area and 2.1 ± 0.6 h to harvest 2352 ± 599 FUs from the beard area. The transection rate for occipital FUs and beard FUs was 3.7 ± 0.4 and 3.9 ± 0.2%, respectively. Completion of the operation took approximately 10.0 ± 0.9 h, and no serious complications were reported 5 days after the procedure. An FU survival rate of 95.7 ± 1.6% was observed at 9 months after transplantation, with no visible hypopigmented scars observed in the bare areas. All patients were satisfied with the resulting cosmetic appearance.</p><p><strong>Conclusion: </strong>Large-scale beard extraction, when combined with occipital hair extraction, is a safe and effective treatment to enhance the cosmetic appearance of East Asian men with advanced AGA.</p>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"7 1","pages":"151-161"},"PeriodicalIF":3.4,"publicationDate":"2020-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6994566/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"81728823","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Exploring substituent diversity of deoxynojirimycin–triazole hybrid iminosugars: Discovery of potent glucosidase inhibitors","authors":"Lin Wang ,&nbsp;Zhijie Fang","doi":"10.1080/07328303.2020.1837150","DOIUrl":"10.1080/07328303.2020.1837150","url":null,"abstract":"<div><p>A series of deoxynojirimycin-triazole hybrid iminosugars had been prepared and investigated against a panel of glucosidases. Compound <strong>10f</strong> (IC₅₀ = 0.063<!--> <!-->±<!--> <!-->0.006 mM) exhibited improved inhibitory potency against α-glucosidase compared to 1-deoxynojirimycin (IC₅₀ = 0.155<!--> <!-->±<!--> <!-->0.015 mM). Moreover, analysis of the kinetics of enzyme inhibition by using Lineweaver–Burk plots indicated that <strong>10f</strong> inhibited α-glucosidase in a competitive manner. Compound <strong>10m</strong> displayed moderate inhibition of α-glucosidase and β-glucosidase. The structure-activity relationships indicated that the introduction of the phenyl group and the nature of 4-position substituents on the phenyl ring had significant effects on the glucosidase inhibitory potency of the compounds.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"39 8","pages":"Pages 415-436"},"PeriodicalIF":1.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2020.1837150","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42871909","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"A mild and convenient approach for selective acetonide cleavage involved in carbohydrate synthesis using PPA-SiO2","authors":"Rahul R. Nikam ,&nbsp;Kiran R. Gore","doi":"10.1080/07328303.2019.1708374","DOIUrl":"10.1080/07328303.2019.1708374","url":null,"abstract":"<div><p>Here, we report a highly selective, efficient and rapid method for the selective cleavage of primary acetonide using silica supported polyphosphoric acid (PPA-SiO₂) for various carbohydrate substrates. Corresponding diols were obtained in good to excellent yields within 30 min using PPA-SiO₂. Overall, PPA-SiO₂ was found to be a useful catalyst for selective acetonide cleavage in carbohydrate substrates which may expand its utility in organic synthesis.</p></div>","PeriodicalId":15311,"journal":{"name":"Journal of Carbohydrate Chemistry","volume":"39 2","pages":"Pages 63-74"},"PeriodicalIF":1.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328303.2019.1708374","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45647990","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}