A general and stereoselective route to α- or β- galactosphingolipids via a common four-carbon building block

Pamela Matto; Emilia Modica; Laura Franchini; Federica Facciotti; Lucia Mori; Gennaro De Libero; Grazia Lombardi; Silvia Fallarini; Luigi Panza; Federica Compostella; Fiamma Ronchetti

doi:10.1021/jo070849z

A general and stereoselective route to α- or β- galactosphingolipids via a common four-carbon building block

Pamela Matto, Emilia Modica, Laura Franchini, Federica Facciotti, Lucia Mori, Gennaro De Libero, Grazia Lombardi, Silvia Fallarini, Luigi Panza, Federica Compostella, Fiamma Ronchetti

Dipartimento di Scienze del Farmaco

Risultato della ricerca: Contributo su rivista › Articolo in rivista › peer review

Abstract

(Chemical Equation Presented) A general synthetic strategy toward α- or β-galactosylceramides and their analogues from 3-azido-2-O-benzyl-1-O- (4-methoxybenzyl)butane-1,2,4-triol is described. The key steps for the installation of the main lipid chain are either a diasteroselective alkynylation reaction yielding the 4R stereocenter of phytosphingosine or a Wittig olefination generating the trans double bond of sphingosine. The methodology allows the preparation of different glycolipids with variations in the structure of the sphingoid base. In particular, three α-GalCer-related compounds have been synthesized and evaluated for their ability to activate CD1d-restricted T-cells.

Lingua originale	Inglese
pagine (da-a)	7757-7760
Numero di pagine	4
Rivista	Journal of Organic Chemistry
Volume	72
Numero di pubblicazione	20
DOI	https://doi.org/10.1021/jo070849z
Stato di pubblicazione	Pubblicato - 28 set 2007

Accesso al documento

10.1021/jo070849z

Altri file e collegamenti

Link to publication in Scopus

Cita questo

@article{d79746e93c844a4aa6ff5f08c5b316f2,

title = "A general and stereoselective route to α- or β- galactosphingolipids via a common four-carbon building block",

abstract = "(Chemical Equation Presented) A general synthetic strategy toward α- or β-galactosylceramides and their analogues from 3-azido-2-O-benzyl-1-O- (4-methoxybenzyl)butane-1,2,4-triol is described. The key steps for the installation of the main lipid chain are either a diasteroselective alkynylation reaction yielding the 4R stereocenter of phytosphingosine or a Wittig olefination generating the trans double bond of sphingosine. The methodology allows the preparation of different glycolipids with variations in the structure of the sphingoid base. In particular, three α-GalCer-related compounds have been synthesized and evaluated for their ability to activate CD1d-restricted T-cells.",

author = "Pamela Matto and Emilia Modica and Laura Franchini and Federica Facciotti and Lucia Mori and {De Libero}, Gennaro and Grazia Lombardi and Silvia Fallarini and Luigi Panza and Federica Compostella and Fiamma Ronchetti",

year = "2007",

month = sep,

day = "28",

doi = "10.1021/jo070849z",

language = "English",

volume = "72",

pages = "7757--7760",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "20",

}

TY - JOUR

T1 - A general and stereoselective route to α- or β- galactosphingolipids via a common four-carbon building block

AU - Matto, Pamela

AU - Modica, Emilia

AU - Franchini, Laura

AU - Facciotti, Federica

AU - Mori, Lucia

AU - De Libero, Gennaro

AU - Lombardi, Grazia

AU - Fallarini, Silvia

AU - Panza, Luigi

AU - Compostella, Federica

AU - Ronchetti, Fiamma

PY - 2007/9/28

Y1 - 2007/9/28

N2 - (Chemical Equation Presented) A general synthetic strategy toward α- or β-galactosylceramides and their analogues from 3-azido-2-O-benzyl-1-O- (4-methoxybenzyl)butane-1,2,4-triol is described. The key steps for the installation of the main lipid chain are either a diasteroselective alkynylation reaction yielding the 4R stereocenter of phytosphingosine or a Wittig olefination generating the trans double bond of sphingosine. The methodology allows the preparation of different glycolipids with variations in the structure of the sphingoid base. In particular, three α-GalCer-related compounds have been synthesized and evaluated for their ability to activate CD1d-restricted T-cells.

AB - (Chemical Equation Presented) A general synthetic strategy toward α- or β-galactosylceramides and their analogues from 3-azido-2-O-benzyl-1-O- (4-methoxybenzyl)butane-1,2,4-triol is described. The key steps for the installation of the main lipid chain are either a diasteroselective alkynylation reaction yielding the 4R stereocenter of phytosphingosine or a Wittig olefination generating the trans double bond of sphingosine. The methodology allows the preparation of different glycolipids with variations in the structure of the sphingoid base. In particular, three α-GalCer-related compounds have been synthesized and evaluated for their ability to activate CD1d-restricted T-cells.

UR - http://www.scopus.com/inward/record.url?scp=34848902594&partnerID=8YFLogxK

U2 - 10.1021/jo070849z

DO - 10.1021/jo070849z

M3 - Article

SN - 0022-3263

VL - 72

SP - 7757

EP - 7760

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 20

ER -

A general and stereoselective route to α- or β- galactosphingolipids via a common four-carbon building block

Abstract

Accesso al documento

Altri file e collegamenti

Fingerprint

Cita questo