No TitleDirect Synthesis of Glycans Containing Challenging ManNAcA Residues

Catherine Alex; Alexei Demchenko

doi:10.1021/acs.joc.1c02351

No TitleDirect Synthesis of Glycans Containing Challenging ManNAcA Residues

Catherine Alex, Alexei Demchenko

University of Missouri-St. Louis

Research output: Contribution to journal › Article › peer-review

Abstract

A method for direct, highly stereoselective synthesis of glycans containing β-linked d-mannosaminuronic acid (ManNAcA) residues is reported herein, among which is the capsular polysaccharide of Staphylococcus aureus type 8. Previous chemical syntheses of this glycan relied on indirect methods comprising glucosylation followed by a multistep epimerization and oxidation sequence. The high β-stereocontrol with direct glycosidation of 3- O -picoloylated ManNAcA donors was achieved using the H-bond-mediated aglycone delivery (HAD) reaction. A method to achieve complete α-ManNAcA stereoselectivity with 3- O -benzoylated donors is also reported.

Original language	American English
Journal	Journal of Organic Chemistry
Volume	87
DOIs	https://doi.org/10.1021/acs.joc.1c02351
State	Published - 2022

Keywords

Aromatic compounds Go to The Journal of Organic Chemistry
Carbohydrates
Ethyl groups
Free radicals
Mixtures

Disciplines

Biochemistry, Biophysics, and Structural Biology

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10.1021/acs.joc.1c02351License: Unspecified

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@article{14946ece375e42f997ec8bbded3982c0,

title = "No TitleDirect Synthesis of Glycans Containing Challenging ManNAcA Residues",

abstract = " A method for direct, highly stereoselective synthesis of glycans containing β-linked d-mannosaminuronic acid (ManNAcA) residues is reported herein, among which is the capsular polysaccharide of Staphylococcus aureus type 8. Previous chemical syntheses of this glycan relied on indirect methods comprising glucosylation followed by a multistep epimerization and oxidation sequence. The high β-stereocontrol with direct glycosidation of 3- O -picoloylated ManNAcA donors was achieved using the H-bond-mediated aglycone delivery (HAD) reaction. A method to achieve complete α-ManNAcA stereoselectivity with 3- O -benzoylated donors is also reported. ",

keywords = "Aromatic compounds Go to The Journal of Organic Chemistry, Carbohydrates, Ethyl groups, Free radicals, Mixtures",

author = "Catherine Alex and Alexei Demchenko",

year = "2022",

doi = "10.1021/acs.joc.1c02351",

language = "American English",

volume = "87",

journal = "Journal of Organic Chemistry",

}

TY - JOUR

T1 - No TitleDirect Synthesis of Glycans Containing Challenging ManNAcA Residues

AU - Alex, Catherine

AU - Demchenko, Alexei

PY - 2022

Y1 - 2022

N2 - A method for direct, highly stereoselective synthesis of glycans containing β-linked d-mannosaminuronic acid (ManNAcA) residues is reported herein, among which is the capsular polysaccharide of Staphylococcus aureus type 8. Previous chemical syntheses of this glycan relied on indirect methods comprising glucosylation followed by a multistep epimerization and oxidation sequence. The high β-stereocontrol with direct glycosidation of 3- O -picoloylated ManNAcA donors was achieved using the H-bond-mediated aglycone delivery (HAD) reaction. A method to achieve complete α-ManNAcA stereoselectivity with 3- O -benzoylated donors is also reported.

AB - A method for direct, highly stereoselective synthesis of glycans containing β-linked d-mannosaminuronic acid (ManNAcA) residues is reported herein, among which is the capsular polysaccharide of Staphylococcus aureus type 8. Previous chemical syntheses of this glycan relied on indirect methods comprising glucosylation followed by a multistep epimerization and oxidation sequence. The high β-stereocontrol with direct glycosidation of 3- O -picoloylated ManNAcA donors was achieved using the H-bond-mediated aglycone delivery (HAD) reaction. A method to achieve complete α-ManNAcA stereoselectivity with 3- O -benzoylated donors is also reported.

KW - Aromatic compounds Go to The Journal of Organic Chemistry

KW - Carbohydrates

KW - Ethyl groups

KW - Free radicals

KW - Mixtures

UR - https://doi.org/10.1021/ACS.JOC.1C02351

U2 - 10.1021/acs.joc.1c02351

DO - 10.1021/acs.joc.1c02351

M3 - Article

VL - 87

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

ER -

No TitleDirect Synthesis of Glycans Containing Challenging ManNAcA Residues

Abstract

Keywords

Disciplines

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