Article
Chemistry, Multidisciplinary
Lifeng Sun, Pradeep Chopra, Geert-Jan Boons
Summary: A new method for the synthesis of heparan sulfate oligosaccharides composed of unsulfonated fragments of different lengths was reported. Competition binding studies showed that the length of the unsulfonated fragment modulates the binding of chemokines.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Ignacio alvarez-Martinez, Colin Ruprecht, Deborah Senf, Hsin-tzu Wang, Breeanna R. Urbanowicz, Fabian Pfrengle
Summary: Plant research is hindered by the lack of pure oligosaccharide samples that accurately represent cell wall glycans. To overcome this, glycosynthases can be used for chemo-enzymatic synthesis of oligosaccharides, allowing coupling reactions between oligosaccharide donors and acceptors. In this study, xylo-oligosaccharides up to dodecasaccharides were synthesized using glycosynthase-mediated coupling reactions. Important enzymes involved in xylan biosynthesis were identified and their activities were studied using biochemical assays.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Jianhong Zhang, Tetsuo Koyama, Takahiko Matsushita, Ken Hatano, Koji Matsuoka
Summary: Efficient synthesis of lauryl thioglycoside of Neu5Gc was achieved from a known thioglycoside of Neu5Ac. The reactivity of Neu5Gc thioglycoside in O-glycosidation was investigated, showing good activities with simple alcohols. The thioglycoside also demonstrated potential as a glycosyl donor in reactions with glucose and lactose derivatives.
TETRAHEDRON LETTERS
(2021)
Article
Biochemistry & Molecular Biology
Viola Kolarikova, Katerina Brodsky, Lucie Petraskova, Helena Pelantova, Josef Cvacka, Libor Havlicek, Vladimir Kren, Katerina Valentova
Summary: Ten phenolic acids were synthesized into their sulfated metabolites using chemoenzymatic and chemical methods. The study also highlighted the importance of counterions in sulfates. These products will be used as standards in metabolic studies and to determine their biological activity.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Multidisciplinary
Pei-Yun Chiang, Avijit K. Adak, Wei-Lun Liang, Chen-Yen Tsai, Hsin-Kai Tseng, Jing-Yan Cheng, Jih Ru Hwu, Alice L. Yu, Jung-Tung Hung, Chun-Cheng Lin
Summary: In this paper, a viable chemoenzymatic method for the synthesis of globo-series GSLs is described. The method allows for the modification of lipid portions of the GSLs, leading to the discovery of lipid-modified Globo H-GSLs with different immunosuppressive activities. This strategy may be applicable to the rapid synthesis of other complex GSLs.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Analytical
Juhi Samal, Tana V. Palomino, Judy Chen, David C. Muddiman, Tatiana Segura
Summary: N-linked glycosylation is a complex protein modification that plays a role in cellular signaling and metabolism. Aberrant protein glycosylation is a characteristic feature of many diseases. Spatial profiling of N-glycans through imaging on tissue sections can be used for disease diagnosis. Infrared matrix-assisted laser desorption electrospray ionization (IR-MALDESI) is a sensitive technique that can be used for mass spectrometry imaging.
ANALYTICAL CHEMISTRY
(2023)
Article
Chemistry, Organic
Pieter de Saint Aulaire, Jorin Hoogenboom, Michiel T. Uiterweerd, Han Zuilhof, Tom Wennekes
Summary: In this study, the synthesis of a carbocyclic sialic acid suitable for activity-based probes (ABPs) was attempted. Although the final conversion into an N-acetylneuraminic acid ABP was not achieved, this work presents a versatile route to potential future carbocyclic sialic acid derivatives.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Hai Yu, Zimin Zheng, Libo Zhang, Xiaohong Yang, Ajit Varki, Xi Chen
Summary: The stable N-acetyl analogues of biologically important 9-O-acetylated b-series gangliosides have been synthesized from a GM3 sphingosine using chemoenzymatic methods. Two chemoenzymatic methods were compared, and the second method was found to be more efficient for synthesizing 9NAc-GD3. Acylation reaction conditions were also improved to obtain target 9-N-acetylated gangliosides in a faster reaction with an easier purification process.
Article
Chemistry, Multidisciplinary
Asuka Shirakawa, Yoshiyuki Manabe, Roberta Marchetti, Kumpei Yano, Seiji Masui, Alba Silipo, Antonio Molinaro, Koichi Fukase
Summary: The fully sialylated tetraantennary N-glycan was synthesized for the first time using a specific strategy, and the synthesized compounds were used to study the recognition mechanism of neuraminidase.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Beata Zdun, Tamara Reiter, Wolfgang Kroutil, Pawel Borowiecki
Summary: We developed chemoenzymatic routes using low-cost starting materials and enzyme preparations to synthesize tenofovir. The key step involved stereoselective reduction or kinetic resolution using alcohol dehydrogenase or lipase as biocatalysts. By employing immobilized lipase in a mixture of vinyl acetate and toluene, the desired (R)-ester was obtained with high yield and optical purity. Alternatively, reduction of a ketone using lyophilized E. coli cells containing recombinant alcohol dehydrogenase resulted in excellent conversion and yield of the corresponding (R)-alcohol. The enzymatic strategy could be applied in the synthesis of tenofovir prodrug derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Alexander Rittner, Mirko Joppe, Jennifer J. Schmidt, Lara Maria Mayer, Simon Reiners, Elia Heid, Dietmar Herzberg, David H. Sherman, Martin Grininger
Summary: This study reports a strategy to introduce fluorine into complex polyketides during biosynthesis. By exchanging a domain of the polyketide synthase, the ability to incorporate fluorine during polyketide chain extension was achieved. The results demonstrate the potential application of this method in the chemoenzymatic synthesis of fluorinated compounds.
Article
Biochemistry & Molecular Biology
Jeremias E. G. A. Dold, Valentin Wittmann
Summary: Metabolic glycoengineering (MGE) is a method utilized to incorporate chemical reporter groups into cellular glycans, allowing for visualization and isolation of glycans and potentially targeting drugs to cancer cells. The study introduced a new labeling reaction using 1,2-diamino-4,5-methylenedioxybenzene for quantification of sialic acid derivates after MGE. It also explored the effects of various ManNAc derivatives on sialic acid production in different cell types.
Article
Biochemistry & Molecular Biology
Xiao Zhang, Chong Ou, Huiying Liu, Sunaina Kiran Prabhu, Chao Li, Qiang Yang, Lai-Xi Wang
Summary: The study introduced a versatile and robust chemoenzymatic method for one-pot site-specific functionalization of antibodies, utilizing selectively modified disaccharide oxazoline derivatives as donor substrates. The method enabled direct labeling and functionalization of antibodies without the need for intermediates and enzyme separation, showing potential for applications in antibody-drug conjugation and beyond.
ACS CHEMICAL BIOLOGY
(2021)
Article
Biochemistry & Molecular Biology
Xiao Zhang, Huiying Liu, Jia He, Chong Ou, Thomas C. Donahue, Musleh M. Muthana, Lishan Su, Lai-Xi Wang
Summary: A chemoenzymatic method enables efficient and site-specific conjugation of high-affinity M6P glycan ligands to antibodies, resulting in structurally well-defined antibody-M6P glycan conjugates. This method has potential applications for targeted degradation of membrane-associated proteins.
ACS CHEMICAL BIOLOGY
(2022)
Article
Chemistry, Organic
Evan O. Romero, Jonathan C. Perkins, Jessica E. Burch, David A. Delgadillo, Hosea M. Nelson, Alison R. H. Narayan
Summary: The first asymmetric synthesis of the pentacyclic fungal marine natural product Xyloketal B is described using a chemoenzymatic strategy. The approach utilizes a biocatalytic benzylic hydroxylation and a [4 + 2] cycloaddition to access key intermediates enroute to (+)-xyloketal B. MicroED is used to confirm the relative configuration of an intermediate, and a reductive approach is employed to access a second key intermediate, culminating in the stereoselective synthesis of (+)-xyloketal B.
