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Literature DB >> 23241945

Chemoenzymatic synthesis of mono- and di-fluorinated Thomsen-Friedenreich (T) antigens and their sialylated derivatives.

Jun Yan¹, Xi Chen, Fengshan Wang, Hongzhi Cao.

Abstract

Fluorinated Thomsen-Friedenreich (T) antigens were synthesized efficiently from chemically produced fluorinated monosaccharides using a highly efficient one-pot two-enzyme chemoenzymatic approach containing a galactokinase and a D-galactosyl-β1-3-N-acetyl-D-hexosamine phosphorylase. These fluorinated T-antigens were further sialylated to form fluorinated ST-antigens using a one-pot two-enzyme system containing a CMP-sialic acid synthetase and an α-2-3-sialyltransferase.

Entities: Chemical Disease Gene Species

Mesh：

Substances：

Year: 2012 PMID： 23241945 PMCID： PMC3616747 DOI： 10.1039/c2ob26989a

Source DB: PubMed Journal: Org Biomol Chem ISSN： 1477-0520 Impact factor: 3.876

24 in total

1. Recent advances in o-sialylation.

Authors: G J Boons; A V Demchenko
Journal: Chem Rev Date: 2000-12-13 Impact factor: 60.622

2. Antibody recognition of fluorinated MUC1 glycopeptide antigens.

Authors: Thomas Oberbillig; Christian Mersch; Sarah Wagner; Anja Hoffmann-Röder
Journal: Chem Commun (Camb) Date: 2011-10-10 Impact factor: 6.222

3. Expression of CD176 (Thomsen-Friedenreich antigen) on lung, breast and liver cancer-initiating cells.

Authors: Wei-Ming Lin; Uwe Karsten; Steffen Goletz; Ruo-Chuan Cheng; Yi Cao
Journal: Int J Exp Pathol Date: 2010-11-11 Impact factor: 1.925

4. A multifunctional Pasteurella multocida sialyltransferase: a powerful tool for the synthesis of sialoside libraries.

Authors: Hai Yu; Harshal Chokhawala; Rebekah Karpel; Hui Yu; Bingyuan Wu; Jianbo Zhang; Yingxin Zhang; Qiang Jia; Xi Chen
Journal: J Am Chem Soc Date: 2005-12-21 Impact factor: 15.419

5. Enzymatic synthesis of fluorinated mechanistic probes for sialidases and sialyltransferases.

Authors: Harshal A Chokhawala; Hongzhi Cao; Hai Yu; Xi Chen
Journal: J Am Chem Soc Date: 2007-08-14 Impact factor: 15.419

6. Chemo-enzymatic synthesis of fluorinated sugar nucleotide: useful mechanistic probes for glycosyltransferases.

Authors: M D Burkart; S P Vincent; A Düffels; B W Murray; S V Ley; C H Wong
Journal: Bioorg Med Chem Date: 2000-08 Impact factor: 3.641

Review 7. Synthetic routes to thiooligosaccharides and thioglycopeptides.

Authors: Kandasamy Pachamuthu; Richard R Schmidt
Journal: Chem Rev Date: 2006-01 Impact factor: 60.622

8. Synthesis of fluorinated mucin core 2 branched oligosaccharides with the potential of novel substrates and enzyme inhibitors for glycosyltransferases and sulfotransferases.

Authors: Jie Xia; Jun Xue; Robert D Locke; E V Chandrasekaran; T Srikrishnan; Khushi L Matta
Journal: J Org Chem Date: 2006-05-12 Impact factor: 4.354

Chemoenzymatic synthesis of mono- and di-fluorinated Thomsen-Friedenreich (T) antigens and their sialylated derivatives.

1. Recent advances in o-sialylation.

2. Antibody recognition of fluorinated MUC1 glycopeptide antigens.

3. Expression of CD176 (Thomsen-Friedenreich antigen) on lung, breast and liver cancer-initiating cells.

4. A multifunctional Pasteurella multocida sialyltransferase: a powerful tool for the synthesis of sialoside libraries.

5. Enzymatic synthesis of fluorinated mechanistic probes for sialidases and sialyltransferases.

6. Chemo-enzymatic synthesis of fluorinated sugar nucleotide: useful mechanistic probes for glycosyltransferases.

Review 7. Synthetic routes to thiooligosaccharides and thioglycopeptides.

8. Synthesis of fluorinated mucin core 2 branched oligosaccharides with the potential of novel substrates and enzyme inhibitors for glycosyltransferases and sulfotransferases.

Review 9. The sweet and sour of cancer: glycans as novel therapeutic targets.

Review 10. MUC1 and the MUCs: a family of human mucins with impact in cancer biology.

1. Efficient chemoenzymatic synthesis of novel galacto-N-biose derivatives and their sialylated forms.

2. One-pot multienzyme (OPME) systems for chemoenzymatic synthesis of carbohydrates.

Review 3. Enzymatic synthesis using glycoside phosphorylases.