Fine Chemicals Angeles Farrań,† Chao Cai,‡ Manuel Sandoval, Yongmei Xu, Jian Liu, María J. Hernaíz,* and Robert J. Linhardt* †Departamento de Química Orgańica y Bio-Orgańica, Facultad de Ciencias, Universidad Nacional de Educacioń a Distancia, Paseo Senda del Rey 4, 28040 Madrid, Spain ‡Key Laboratory of Marine Drugs of Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China Escuela de Química, Universidad Nacional of Costa Rica, Post Office Box 86, 3000 Heredia, Costa Rica Division of Chemical Biology and Medicinal Chemistry, Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina 27599, United States Center for Biotechnology & Interdisciplinary Studies and Department of Chemistry & Chemical Biology, Rensselaer Polytechnic Institute, Biotechnology Center 4005, Troy, New York 12180, United States Departamento de Química Orgańica y Farmaceútica, Facultad de Farmacia, Universidad Complutense de Madrid, Pz/Ramoń y Cajal s/n, 28040 Madrid, Spain

Green solvents in carbohydrate chemistry: from raw materials to fine chemicals.

This review is the fourth update of the original review, published in 1999, on the application of MALDI mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2006. The review covers fundamental studies, fragmentation of carbohydrate ions, method developments, and applications of the technique to the analysis of different types of carbohydrate. Specific compound classes that are covered include carbohydrate polymers from plants, N- and O-linked glycans from glycoproteins, glycated proteins, glycolipids from bacteria, glycosides, and various other natural products. There is a short section on the use of MALDI-TOF mass spectrometry for the study of enzymes involved in glycan processing, a section on industrial processes, particularly the development of biopharmaceuticals and a section on the use of MALDI–MS to monitor products of chemical synthesis of carbohydrates. Large carbohydrate–protein complexes and glycodendrimers are highlighted in this final section. © 2010 Wiley Periodicals, Inc., Mass Spec Rev 30:1–100, 2011

Analysis of carbohydrates and glycoconjugates by matrix-assisted laser desorption/ionization mass spectrometry: an update for the period 2005-2006.

The past few decades have seen a renewed interest in the chemical synthesis of oligosaccharides, owing to increased recognition of their biological importance. Of the different approaches to oligosaccharides, solid-phase synthesis has emerged as a particularly attractive option, due in large part to its potential for automation. This perspective describes principles to consider when planning solid-phase oligosaccharide synthesis (SPOS), including recent achievements and areas where future work is necessary.

Principles of modern solid-phase oligosaccharide synthesis.

Combinatorial ionic catch-and-release oligosaccharide synthesis (combi-ICROS).

Carbohydrates are important raw materials in the chemical industry and they also play significant roles in biological systems. Ionic liquids (ILs), the promising and designable green solvents, have been proposed as an alternative to traditional organic solvents. In light of their unique physicochemical properties, ILs have a good many applications for carbohydrates. This review provides a compilation on the main results achieved by application of ILs for carbohydrates in both separation and analytical chemistry. The IL-based solid-liquid and liquid-liquid separation processes for carbohydrates (especially for those with high molecular weights), such as carbohydrate isolation from biomass, IL-based aqueous biphasic systems (ABSs), selective precipitation, support tags for purification, and analytical techniques, such as matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS), electrospray ionization mass spectrometry (ESI-MS), nuclear magnetic resonance (NMR), high performance liquid chromatography (HPLC), among others, are here reviewed. Key accomplishments and future perspectives in this field are discussed.

Application of ionic liquids in separation and analysis of carbohydrates: State of the art and future trends

An improved method for the synthesis of large and complex oligosaccharides on ionic liquid (IL) support was developed. A strategy to attach the acceptor on IL using a more stable ether linker was used to prevent undesirable decomposition and side products. A “dissolution–evaporation–precipitation” purification procedure was also developed by combining the advantages of precipitation and solid–liquid extraction to reduce mechanical loss and purification time. This approach was successfully used for the rapid assembly of ionic liquid supported homolinear α(1→2)-linked nonamannoside in 25.2% overall yield within 28.5 h.

Assembly of homolinear α(1→2)-linked nonamannoside on ionic liquid support.

The invention discloses a method for chemically synthesizing natural product salidroside In the method, lewis acid serving as a catalyst, tyrosol of acyl protected phenolic hydroxyl serving as a glycosylation receptor, and beta-D-5 acetyl glucose serving as glycosylation donor perform a glycosylation reaction to obtain 1-[2-(4-acyloxy phenyl) ethyl]-2,3,4,6-O-tetraacetyl-beta-D-glucopyranoside; and acyl protecting group is removed in an alkaline condition to obtain salidroside Compared with the traditional method, the method has easily available raw materials, the glycosylation receptor, the glycosylation product and the final product can be prepared through recrystallization, column chromatography and other purification processes are eliminated, the reaction step is short, the preparation process is simple, the glycosylation reaction catalyst has low cost and is easily available, so that the preparation cost is remarkably reduced; and a heavy metal salt catalyst is not used in the reaction, so that the synthesis product is more suitable to be used as a raw material of medicaments and health-care products The method is suitable for industrial production of salidroside

Salidroside chemical synthesis method for industrialization

An efficient ionic liquid supported divergent assembly of 3,6-branched glucosamine-containing pentasaccharide

Method for rapidly preparing oligosaccharide by using ionic liquid load and immediate compound thereof

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Papers

Assembly of homolinear α(1→2)-linked nonamannoside on ionic liquid support.

Salidroside chemical synthesis method for industrialization

An efficient ionic liquid supported divergent assembly of 3,6-branched glucosamine-containing pentasaccharide

Method for rapidly preparing oligosaccharide by using ionic liquid load and immediate compound thereof