15548-45-5Relevant articles and documents
Glycosylation in room temperature ionic liquid using unprotected and unactivated donors
Park, Tae-Joon,Weiwer, Michel,Yuan, Xuejun,Baytas, Sultan N.,Munoz, Eva M.,Murugesan, Saravanababu,Linhardt, Robert J.
, p. 614 - 620 (2007)
Glycosylation in room temperature ionic liquid is demonstrated using unprotected and unactivated donors. Modest yields of simple benzyl glycosides and disaccharides of glucose, mannose and N-acetylgalactosamine were obtained in 1-ethyl-3-methylimidazolium benzoate with Amberlite IR-120 (H+) resin or p-toluenesulfonic acid as promoters.
Anomeric alkylations and acylations of unprotected mono- and disaccharides mediated by pyridoneimine in aqueous solutions
Dey, Kalyan,Jayaraman, Narayanaswamy
supporting information, p. 2224 - 2227 (2022/02/17)
A site-specific deprotonation followed by alkylations and acylations of sugar hemiacetals to the corresponding alkyl glycosides and acylated sugars in aqueous solutions is disclosed herein. Pyridoneimine as a new base is developed to mediate the deprotonation of readily available sugar hemiacetals and further reactions with alkylation and acylation agents.
Rhamnogalacturonan II: Chemical Synthesis of a Substructure Including α-2,3-Linked Kdo**
Mancuso, Enzo,Romanò, Cecilia,Trattnig, Nino,Gritsch, Philipp,Kosma, Paul,Clausen, Mads H.
, p. 7099 - 7102 (2021/04/19)
The synthesis of a fully deprotected Kdo-containing rhamnogalacturonan II pentasaccharide is described. The strategy relies on the preparation of a suitably protected homogalacturonan tetrasaccharide backbone, through a post-glycosylation oxidation approach, and its stereoselective glycosylation with a Kdo fluoride donor.
Multi-gram scale synthesis of a bleomycin (BLM) carbohydrate moiety: exploring the antitumor beneficial effect of BLM disaccharide attached to 10-hydroxycamptothecine (10-HCPT)
Li, MaoLin,Huang, Weiping,Jiang, Zhilin,Shi, Yonghui,Yuan, Sisi,Fu, Kaishuo,Chen, YongJun,Zhou, Li,Zhou, Wen
, p. 6010 - 6020 (2019/04/17)
The “tumor-seeking” role of bleomycin (BLM) disaccharide has been demonstrated to serve as a promising tool for cancer diagnosis and a potential ligand for targeted therapy. However, these practical applications are often hampered by the lack of BLM disaccharide. Herein, an efficient multi-gram synthesis of peracetylated BLM disaccharide 20 is achieved by a TMSOTF-mediated glycosidation coupling manner in 43.6% overall yield in terms of benzyl galactoside. The critical innovation of the synthetic strategy is that inexpensive benzyl galactoside was first adopted to prepare an l-gulose subunit 3 as a glycosyl acceptor, with a much shorter route in 73.0% yield, and a 3-O-carbamoyl-mannose donor 4 was achieved in 47.2% yield by lowering the amount of dibutyltin oxide, and merging aminolysis and selective deacetylation into a one-pot reaction. Next, the incorporation of BLM disaccharide into 10-hydroxycamptothecin (10-HCPT), a non-specific model compound, to form conjugate 1 could significantly improve the antitumor activity and display obvious selectivity toward cancerous and normal cells in comparison with 10-HCPT. Moreover, BLM disaccharide itself was non-cytotoxic, clearly indicating the importance and potential of BLM disaccharide in solving the targeted antitumor therapy of cytotoxic drugs.
INHIBITORS OF HEXOKINASE AND METHODS OF USE THEREOF
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Page/Page column 77; 78, (2018/09/25)
Provided herein are substituted substituted heterocycles useful as inhibitors of the HKII enzyme. The invention further provides pharmaceutical compositions of the compounds of the invention. The invention further provides medical uses of substituted heterocycles, for example, as antitumor agents.
Preparation methods of 2-hydroxygulose receptor derivative, bleomycin disaccharide and precursor of bleomycin disaccharide
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Paragraph 0050-0057; 0076-0080; 0090-0094, (2019/01/08)
The invention discloses a preparation method of a 2-hydroxygulose receptor derivative. The method comprises the following steps: carrying out a series of reactions of ylidene protection on benzyl-beta-galactoside, 3-position configuration inversion, deacetylation, and selective acetylation. Meanwhile, the invention also discloses a method for preparing bleomycin disaccharide and a precursor of bleomycin disaccharide by using the 2-hydroxygulose receptor derivative prepared by the method as a receptor. According to the invention, through the adoption of the preparation method of the 2-hydroxygulose receptor derivative, the problems that sources of natural L-gulose are rare, cost is too high, and industrialization is not facilitated and the like are solved; meanwhile, the problems that the bleomycin disaccharide and the precursor of the bleomycin disaccharide are low in yield, reaction operability and repeatability are poor, industrialization is not facilitated and the like are solved. The preparation methods have the advantages that raw materials are cheap and easily available, the yield is high, the operability is high, conditions can be easily controlled, industrial amplificationcan be realized, efficiency is high, cost is low, and the like.
Glycosylated Platinum(IV) Complexes as Substrates for Glucose Transporters (GLUTs) and Organic Cation Transporters (OCTs) Exhibited Cancer Targeting and Human Serum Albumin Binding Properties for Drug Delivery
Ma, Jing,Wang, Qingpeng,Huang, Zhonglv,Yang, Xiande,Nie, Quandeng,Hao, Wenpei,Wang, Peng George,Wang, Xin
supporting information, p. 5736 - 5748 (2017/07/22)
Glycosylated platinum(IV) complexes were synthesized as substrates for GLUTs and OCTs for the first time, and the cytotoxicity and detailed mechanism were determined in vitro and in vivo. Galactoside Pt(IV), glucoside Pt(IV), and mannoside Pt(IV) were highly cytotoxic and showed specific cancer-targeting properties in vitro and in vivo. Glycosylated platinum(IV) complexes 5, 6, 7, and 8 (IC50 0.24-3.97 μM) had better antitumor activity of nearly 166-fold higher than the positive controls cisplatin (1a), oxaliplatin (3a), and satraplatin (5a). The presence of a hexadecanoic chain allowed binding with human serum albumin (HSA) for drug delivery, which not only enhanced the stability of the inert platinum(IV) prodrugs but also decreased their reduction by reductants present in human whole blood. Their preferential accumulation in cancer cells compared to noncancerous cells (293T and 3T3 cells) suggested that they were potentially safe for clinical therapeutic use.
Direct glycosylation of bioactive small molecules with glycosyl iodide and strained olefin as acid scavenger
Gu, Xiangying,Chen, Lin,Wang, Xin,Liu, Xiao,You, Qidong,Xi, Wenwei,Gao, Li,Chen, Guohua,Chen, Yue-Lei,Xiong, Bing,Shen, Jingkang
, p. 1100 - 1110 (2014/03/21)
A new strategy for diversity-oriented direct glycosylation of bioactive small molecules was developed. This reaction features (-)-β-pinene as acid scavenger and work with glycosyl iodides under mild conditions. With the aid of RP-HPLC and chiral SFC separation techniques, the new direct glycosylation proved effective at gram scale on bioactive small molecules including AZD6244, podophyllotoxin, paclitaxel, and docetaxel. Interesting glycoside derivatives were efficiently created with good yields and 1,2-cis selectivity.
Chemoenzymatic synthesis of ADP-d-glycero-β-d-manno-heptose and study of the substrate specificity of HldE
Li, Tiehai,Wen, Liuqing,Williams, Adriel,Wu, Baolin,Li, Lei,Qu, Jingyao,Meisner, Jeffrey,Xiao, Zhongying,Fang, Junqiang,Wang, Peng George
, p. 1139 - 1147 (2014/02/14)
An efficient one-pot three enzymes strategy for chemoenzymatic synthesis of ADP-d-glycero-β-d-manno-heptose (ADP-d, d-heptose) was reported using chemically synthesized d, d-heptose-7-phosphate and the ADP-d, d-heptose biosynthetic enzymes HldE and GmhB M
1,2-cis Alkyl glycosides: Straightforward glycosylation from unprotected 1-thioglycosyl donors
Meng, Bo,Zhu, Zhenqian,Baker, David C.
, p. 5182 - 5191 (2014/07/08)
A 1,2-cis-alkyl glycosidation protocol that makes use of unprotected phenyl 1-thioglycosyl donors is reported. Glycosylation of various functionalized alcohols was accomplished in moderate to high yield and selectivity to give the 1,2-cis-glycosides. In order to quickly develop optimum glycosylation conditions, an FIA (flow injection analysis)-ESI-TOF-MS method was developed that enabled rapid and quantitative evaluation of yield on small scale. This methodology, coupled with NMR spectroscopy, allowed for rapid evaluation of the overall reactions.
