A versatile approach to the synthesis of glycans containing mannuronic acid residues

Catherine Alex; Satsawat Visansirikul; Alexei Demchenko

doi:10.1039/D1OB00188D

A versatile approach to the synthesis of glycans containing mannuronic acid residues

Catherine Alex, Satsawat Visansirikul, Alexei Demchenko

University of Missouri-St. Louis

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

Abstract

Reported herein is a new method for a highly effective synthesis of β-glycosides from mannuronic acid donors equipped with the 3- O -picoloyl group. The stereocontrol of glycosylations was achieved by means of the H-bond-mediated aglycone delivery (HAD). The method was utilized for the synthesis of a tetrasaccharide linked via β-(1 → 3)-mannuronic linkages. We have also investigated 3,6-lactonized glycosyl donors that provided moderate to high β-manno stereoselectivity in glycosylations. A method to achieve complete α-manno stereoselectivity with mannuronic acid donors equipped with 3- O -benzoyl group is also reported.

Original language	American English
Journal	Organic and Biomolecular Chemistry
DOIs	https://doi.org/10.1039/D1OB00188D
State	Published - 2021

Disciplines

Biochemistry, Biophysics, and Structural Biology

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title = "A versatile approach to the synthesis of glycans containing mannuronic acid residues",

abstract = " Reported herein is a new method for a highly effective synthesis of β-glycosides from mannuronic acid donors equipped with the 3- O -picoloyl group. The stereocontrol of glycosylations was achieved by means of the H-bond-mediated aglycone delivery (HAD). The method was utilized for the synthesis of a tetrasaccharide linked via β-(1 → 3)-mannuronic linkages. We have also investigated 3,6-lactonized glycosyl donors that provided moderate to high β-manno stereoselectivity in glycosylations. A method to achieve complete α-manno stereoselectivity with mannuronic acid donors equipped with 3- O -benzoyl group is also reported. ",

author = "Catherine Alex and Satsawat Visansirikul and Alexei Demchenko",

note = "Reported herein is a new method for a highly effective synthesis of β-glycosides from mannuronic acid donors equipped with the 3-O-picoloyl group. The stereocontrol of glycosylations was achieved by means of the H-bond-mediated aglycone delivery (HAD). The method was utilized for the synthesis of a tetrasacc",

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doi = "10.1039/D1OB00188D",

language = "American English",

journal = "Organic and Biomolecular Chemistry",

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T1 - A versatile approach to the synthesis of glycans containing mannuronic acid residues

AU - Alex, Catherine

AU - Visansirikul, Satsawat

AU - Demchenko, Alexei

N1 - Reported herein is a new method for a highly effective synthesis of β-glycosides from mannuronic acid donors equipped with the 3-O-picoloyl group. The stereocontrol of glycosylations was achieved by means of the H-bond-mediated aglycone delivery (HAD). The method was utilized for the synthesis of a tetrasacc

PY - 2021

Y1 - 2021

N2 - Reported herein is a new method for a highly effective synthesis of β-glycosides from mannuronic acid donors equipped with the 3- O -picoloyl group. The stereocontrol of glycosylations was achieved by means of the H-bond-mediated aglycone delivery (HAD). The method was utilized for the synthesis of a tetrasaccharide linked via β-(1 → 3)-mannuronic linkages. We have also investigated 3,6-lactonized glycosyl donors that provided moderate to high β-manno stereoselectivity in glycosylations. A method to achieve complete α-manno stereoselectivity with mannuronic acid donors equipped with 3- O -benzoyl group is also reported.

AB - Reported herein is a new method for a highly effective synthesis of β-glycosides from mannuronic acid donors equipped with the 3- O -picoloyl group. The stereocontrol of glycosylations was achieved by means of the H-bond-mediated aglycone delivery (HAD). The method was utilized for the synthesis of a tetrasaccharide linked via β-(1 → 3)-mannuronic linkages. We have also investigated 3,6-lactonized glycosyl donors that provided moderate to high β-manno stereoselectivity in glycosylations. A method to achieve complete α-manno stereoselectivity with mannuronic acid donors equipped with 3- O -benzoyl group is also reported.

UR - https://doi.org/10.1039/D1OB00188D

U2 - 10.1039/D1OB00188D

DO - 10.1039/D1OB00188D

M3 - Article

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

ER -

A versatile approach to the synthesis of glycans containing mannuronic acid residues

Abstract

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