Literature DB >> 11273599

Total syntheses of tumor-related antigens N3: probing the feasibility limits of the glycal assembly method.

H M Kim1, I J Kim, S J Danishefsky.   

Abstract

The total syntheses of two octasaccharide antigens isolated from human milk, 1 and 2, and their corresponding allyl glycosides, 3 and 4, have been achieved by utilizing the glycal method. Convergent assembly of the core hexasaccharides and concurrent introduction of two alpha-L-fucosyl moieties at the late stage of the syntheses provided these complex carbohydrates in a concise manner. With synthetic material obtained, biological evaluations of these antigens as potential gastrointestinal cancer immunotherapeutic agents have been initiated.

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Year:  2001        PMID: 11273599     DOI: 10.1021/ja0022730

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  9 in total

1.  Synthesis of the Non-Reducing Hexasaccharide Fragment of Saccharomicin B.

Authors:  Manas Jana; Clay S Bennett
Journal:  Org Lett       Date:  2018-11-14       Impact factor: 6.005

Review 2.  Expeditious oligosaccharide synthesis via selective, semi-orthogonal, and orthogonal activation.

Authors:  Sophon Kaeothip; Alexei V Demchenko
Journal:  Carbohydr Res       Date:  2011-05-18       Impact factor: 2.104

3.  Divergent heparin oligosaccharide synthesis with preinstalled sulfate esters.

Authors:  Gopinath Tiruchinapally; Zhaojun Yin; Mohammad El-Dakdouki; Zhen Wang; Xuefei Huang
Journal:  Chemistry       Date:  2011-07-22       Impact factor: 5.236

4.  Chemoenzymatic Synthesis of Asymmetrically Branched Human Milk Oligosaccharide Lacto-N-Hexaose.

Authors:  Kai-Eng Ooi; Xiu-Wen Zhang; Cheng-Yu Kuo; Ying-Jia Liu; Ching-Ching Yu
Journal:  Front Chem       Date:  2022-05-31       Impact factor: 5.545

5.  Rapid de Novo Preparation of 2,6-Dideoxy Sugar Libraries through Gold-Catalyzed Homopropargyl Orthoester Cyclization.

Authors:  Subbarao Yalamanchili; William Miller; Xizhao Chen; Clay S Bennett
Journal:  Org Lett       Date:  2019-11-22       Impact factor: 6.005

6.  Tailoring chemoenzymatic oxidation via in situ peracids.

Authors:  Rebecca N Re; Johanna C Proessdorf; James J La Clair; Maeva Subileau; Michael D Burkart
Journal:  Org Biomol Chem       Date:  2019-11-06       Impact factor: 3.876

Review 7.  Chemical O-Glycosylations: An Overview.

Authors:  Rituparna Das; Balaram Mukhopadhyay
Journal:  ChemistryOpen       Date:  2016-08-17       Impact factor: 2.911

Review 8.  Human Milk Oligosaccharides (HMOS): Structure, Function, and Enzyme-Catalyzed Synthesis.

Authors:  Xi Chen
Journal:  Adv Carbohydr Chem Biochem       Date:  2015-11-11       Impact factor: 3.714

9.  Mild Method for 2-Naphthylmethyl Ether Protecting Group Removal Using a Combination of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and β-Pinene.

Authors:  Dina Lloyd; Marissa Bylsma; Danielle K Bright; Xizhao Chen; Clay S Bennett
Journal:  J Org Chem       Date:  2017-03-27       Impact factor: 4.354

  9 in total

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