Synthesis of α-Galactosyl Ceramide (KRN7000) and Analogues Thereof via a Common Precursor and Their Preliminary Biological Assessment

被引：27

作者：

Michieletti, Mario ^{[1
]}

Bracci, Antonio ^{[1
]}

Compostella, Federica ^{[2
]}

De Libero, Gennaro ^{[3
]}

Mori, Lucia ^{[3
]}

Fallarini, Silvia ^{[1
]}

Lombardi, Grazia ^{[1
]}

Panza, Luigi ^{[1
]}

机构：

[1] Univ Piemonte Orientale Amedeo Avogadro, Dipartimento Sci Chim Alimentari Farmaceut & Farm, I-28100 Novara, Italy

[2] Univ Milan, Dipartimento Chim Biochim & Biotecnol Med, I-20133 Milan, Italy

[3] Univ Basel Hosp, Dept Biomed, CH-4031 Basel, Switzerland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 22期

关键词：

D O I：

10.1021/jo8019994

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new practical synthesis of alpha-GalCer and of its analogues is presented, opening the chance to easily modify the sphingosine chain. The common precursor is a disaccharide, obtained by coupling tetra-O-benzyl-D-galactose with allyl 2,3-O-isopropylidene-D-lyxofuranoside. Introduction of alkyl chains via Wittig reaction (for alpha-GalCer and OCH) or via Williamson reaction (for oxa analogues) followed by standard synthetic steps allows one to efficiently obtain such compounds. The analogues are able to activate iNKT cells when presented by CD1d expressing cells.

引用

页码：9192 / 9195

页数：4

共 23 条

[1] Synthesis and biological activity of α-galactosyl ceramide KRN7000 and galactosyl (α1→2) galactosyl ceramide
Veerapen, Natacha
Brigl, Manfred
Garg, Salil
Cerundolo, Vincenzo
Cox, Liam R.
Brenner, Michael B.
Besra, Gurdyal S.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (15) : 4288 - 4291
[2] Synthesis of Hydroxylated Analogues of α-Galactosyl Ceramide (KRN7000) with Varying Stereochemistry
Sawant, Ratnnadeep C.
Hung, Jung-Tung
Chuang, Huei-Lin
Lin, Huan-Shuan
Chen, Wan-Shin
Yu, Alice L.
Luo, Shun-Yuan
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (33) : 7611 - 7623
[3] Synthesis of truncated analogues of the iNKT cell agonist, α-galactosyl ceramide (KRN7000), and their biological evaluation
Veerapen, Natacha
Reddington, Faye
Salio, Mariolina
Cerundolo, Vincenzo
Besra, Gurdyal S.
BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (01) : 221 - 228
[4] Synthesis and biological activity of α-L-fucosyl ceramides, analogues of the potent agonist, α-D-galactosyl ceramide KRN7000
Veerapen, Natacha
Reddington, Faye
Bricard, Gabriel
Porcelli, Steven A.
Besra, Gurdyal S.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (11) : 3223 - 3226
[5] Synthesis and biological activity of hydroxylated analogues of KRN7000 (α-galactosylceramide)
Shiozaki, Masao
Tashiro, Takuya
Koshino, Hiroyuki
Shigeura, Tomokuni
Watarai, Hiroshi
Taniguchi, Masaru
Mori, Kenji
CARBOHYDRATE RESEARCH, 2013, 370 : 46 - 66
[6] Asymmetric Synthesis of the α-D-Galactosyl Ceramide KRN7000 via an Organocatalytic Aldol Reaction as Key Step
Enders, Dieter
Terteryan, Violeta
Palecek, Jiri
SYNTHESIS-STUTTGART, 2010, (17): : 2979 - 2984
[7] Design and synthesis of new KRN7000 analogues
Sun, Man
Wang, Yuhang
Ye, Xin-Shan
TETRAHEDRON, 2013, 69 (35) : 7438 - 7447
[8] Synthesis and biological activity of ester and ether analogues of α-galactosylceramide (KRN7000)
Shiozaki, Masao
Tashiro, Takuya
Koshino, Hiroyuki
Nakagawa, Ryusuke
Inoue, Sayo
Shigeura, Tomokuni
Watarai, Hiroshi
Taniguchi, Masaru
Mori, Kenji
CARBOHYDRATE RESEARCH, 2010, 345 (12) : 1663 - 1684
[9] The total synthesis of the c-glycoside analog of KRN7000, a potent alpha galactosyl ceramide.
Franck, RW
Yang, GG
Schmieg, J
Tsuji, M
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U256 - U256
[10] Synthesis and evaluation of sphinganine analogues of KRN7000 and OCH
Ndonye, RM
Izmirian, DP
Dunn, MF
Yu, KOA
Porcelli, SA
Khurana, A
Kronenberg, M
Richardson, SK
Howell, AR
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (25): : 10260 - 10270

← 1 2 3 →