A Diversity-Oriented Strategy for Chemoenzymatic Synthesis of Glycosphingolipids and Related Derivatives

Qingjiang Li; Mohit Jaiswal; Rajendra S. Rohokale; Zhongwu Guo

doi:10.1021/acs.orglett.0c02847

A Diversity-Oriented Strategy for Chemoenzymatic Synthesis of Glycosphingolipids and Related Derivatives

Qingjiang Li
, Mohit Jaiswal
, Rajendra S. Rohokale
, Zhongwu Guo

Chemistry

University of Florida

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

Abstract

A diversity-oriented strategy combining enzymatic glycan assembly and on-site lipid remodeling via chemoselective cross-metathesis and N-acylation was developed for glycosphingolipid (GSL) synthesis starting from a common, simple glycoside. The strategy was verified with a series of natural GSLs and GSL derivatives and showed several advantages. Most notably, it enabled two-way diversification of the glycan and lipid, including introduction of designed molecular tags, to provide functionalized GSLs useful for biological studies and applications.

Original language	English
Pages (from-to)	8245-8249
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	21
DOIs	https://doi.org/10.1021/acs.orglett.0c02847
State	Published - Nov 6 2020

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.0c02847

Cite this

@article{abdbcbf72b6c4158b4f31a8c2a3ad5f4,

title = "A Diversity-Oriented Strategy for Chemoenzymatic Synthesis of Glycosphingolipids and Related Derivatives",

abstract = "A diversity-oriented strategy combining enzymatic glycan assembly and on-site lipid remodeling via chemoselective cross-metathesis and N-acylation was developed for glycosphingolipid (GSL) synthesis starting from a common, simple glycoside. The strategy was verified with a series of natural GSLs and GSL derivatives and showed several advantages. Most notably, it enabled two-way diversification of the glycan and lipid, including introduction of designed molecular tags, to provide functionalized GSLs useful for biological studies and applications.",

author = "Qingjiang Li and Mohit Jaiswal and Rohokale, \{Rajendra S.\} and Zhongwu Guo",

note = "Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = nov,

day = "6",

doi = "10.1021/acs.orglett.0c02847",

language = "English",

volume = "22",

pages = "8245--8249",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "21",

}

TY - JOUR

T1 - A Diversity-Oriented Strategy for Chemoenzymatic Synthesis of Glycosphingolipids and Related Derivatives

AU - Li, Qingjiang

AU - Jaiswal, Mohit

AU - Rohokale, Rajendra S.

AU - Guo, Zhongwu

PY - 2020/11/6

Y1 - 2020/11/6

N2 - A diversity-oriented strategy combining enzymatic glycan assembly and on-site lipid remodeling via chemoselective cross-metathesis and N-acylation was developed for glycosphingolipid (GSL) synthesis starting from a common, simple glycoside. The strategy was verified with a series of natural GSLs and GSL derivatives and showed several advantages. Most notably, it enabled two-way diversification of the glycan and lipid, including introduction of designed molecular tags, to provide functionalized GSLs useful for biological studies and applications.

AB - A diversity-oriented strategy combining enzymatic glycan assembly and on-site lipid remodeling via chemoselective cross-metathesis and N-acylation was developed for glycosphingolipid (GSL) synthesis starting from a common, simple glycoside. The strategy was verified with a series of natural GSLs and GSL derivatives and showed several advantages. Most notably, it enabled two-way diversification of the glycan and lipid, including introduction of designed molecular tags, to provide functionalized GSLs useful for biological studies and applications.

UR - https://www.scopus.com/pages/publications/85095862282

UR - https://www.scopus.com/pages/publications/85095862282#tab=citedBy

U2 - 10.1021/acs.orglett.0c02847

DO - 10.1021/acs.orglett.0c02847

M3 - Article

C2 - 33074681

AN - SCOPUS:85095862282

SN - 1523-7060

VL - 22

SP - 8245

EP - 8249

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

A Diversity-Oriented Strategy for Chemoenzymatic Synthesis of Glycosphingolipids and Related Derivatives

Abstract

ASJC Scopus Subject Areas

Access to Document

Other files and links

Fingerprint

Cite this