Synthesis of hexaarabinofuranoside bearing the 4-(3-azidopropoxy)phenyl aglycone related to the terminal fragment of polysaccharides of mycobacteria

被引：3

作者：

Abronina, P. I. ^{[1
]}

Malysheva, N. N. ^{[1
]}

Zinin, A. I. ^{[1
]}

Kolotyrkina, N. G. ^{[1
]}

Kononov, L. O. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, 47 Leninsky Prosp, Moscow 119991, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2024年 / 73卷 / 05期

基金：

俄罗斯科学基金会;

关键词：

mycobacteria; Mycobacterium tuberculosis; lipoarabinomannan; arabinogalactan; hexaarabinofuranoside; glycosylation; Janus aglycones; JANUS AGLYCONE; GLYCOSYL DONOR; LIPOARABINOMANNAN; TUBERCULOSIS; ANTIGENS;

D O I：

10.1007/s11172-024-4260-4

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A convergent synthesis alpha-(1 -> 3)-, alpha-(1 -> 5), beta-(1 -> 2)-linked hexaarabinofuranoside related to the terminal fragment of lipoarabinomannan (LAM) and arabinogalactan of mycobacteria as a glycoside with 4-(3-azidopropoxy)phenyl aglycone was accomplished. 4-(3-Azidopropoxy)phenyl aglycone belongs to the class of Janus aglycones, which can be used as both a temporary protective group for the anomeric position of the carbohydrate and a (pre)spacer for the synthesis of neoglycoconjugates. The key step of the synthesis is the formation of 1,2-trans glycosidic linkage with the use of Ara-beta-(1 -> 2)-Ara p-tolylthioarabinofuranoside bearing five triisopropylsilyl groups.

引用

页码：1417 / 1425

页数：9

共 40 条

[1] Synthesis of a tetrasaccharide containing Janus aglycone related to the terminal fragment of polysaccharides of mycobacteria [J].

Abronina, P. I. ;

Malysheva, N. N. ;

Zinin, A. I. ;

Kononov, L. O. .

RUSSIAN CHEMICAL BULLETIN, 2023, 72 (04) :1046-1058

[2] Synthesis of selectively protected α-(1→3)- and α-(1→5)-linked octasaccharide moiety bearing a Janus aglycone, related to the branching site of mycobacterial polysaccharides [J].

Abronina, P. I. ;

Shvyrkina, Yu. S. ;

Zinin, A. I. ;

Chizhov, A. O. ;

Kononov, L. O. .

RUSSIAN CHEMICAL BULLETIN, 2022, 71 (12) :2740-2750

[3] The use of silyl groups in the synthesis of arabinofuranosides [J].

Abronina, P., I ;

Podvalnyy, N. M. ;

Kononov, L. O. .

RUSSIAN CHEMICAL BULLETIN, 2022, 71 (01) :6-29

[4] Synthesis of covalent conjugates of hexaarabinofuranoside with proteins and their testing as antigens for serodiagnosis of tuberculosis [J].

Abronina, P. I. ;

Podvalnyy, N. M. ;

Mel'nikova, T. M. ;

Zinin, A. I. ;

Fedina, K. G. ;

Kachala, V. V. ;

Torgov, V. I. ;

Kononov, L. O. ;

Panfertsev, E. A. ;

Baranova, E. V. ;

Mochalov, V. V. ;

Dyatlova, V. I. ;

Biketov, S. F. .

RUSSIAN CHEMICAL BULLETIN, 2010, 59 (12) :2333-2337

[5] Five Triisopropylsilyl Substituents in Ara-β-(1→2)-Ara Disaccharide Glycosyl Donor Make Unselective Glycosylation Reaction Stereoselective [J].

Abronina, Polina I. ;

Malysheva, Nelly N. ;

Stepanova, Elena V. ;

Shvyrkina, Julia S. ;

Zinin, Alexander I. ;

Kononov, Leonid O. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (46)

[6] Trifluoroacetic Acid Promoted Ring Contraction in 2,3-Di-O-silylated O-Galactopyranosides and Hemiacetals [J].

Abronina, Polina, I ;

Malysheva, Nelly N. ;

Zinin, Alexander, I ;

Karpenko, Maxim Y. ;

Kolotyrkina, Natalya G. ;

Kononov, Leonid O. .

SYNLETT, 2022, 33 (05) :473-477

[7] Unusual Outcome of Glycosylation: Hydrogen-Bond Mediated Control of Stereoselectivity byN-Trifluoroacetyl Group? [J].

Abronina, Polina, I ;

Zinin, Alexander, I ;

Chizhov, Alexander O. ;

Kononov, Leonid O. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (27) :4146-4160

[8] Application of a Janus aglycon with dual function in benzyl-free synthesis of spacer-armed oligosaccharide fragments of polysaccharides from rhizobacterium Azospirillum brasilense sp7 [J].

Abronina, Polina I. ;

Zinin, Alexander I. ;

Romashin, Denis A. ;

Tereshina, Valeria V. ;

Chizhov, Alexander O. ;

Kononov, Leonid O. .

CARBOHYDRATE RESEARCH, 2018, 464 :28-43

[9] A Novel Glycosyl Donor with a Triisopropylsilyl Nonparticipating Group in Benzyl-Free Stereoselective 1,2-cis-Galactosylation [J].

Abronina, Polina I. ;

Zinin, Alexander I. ;

Malysheva, Nelly N. ;

Stepanova, Elena V. ;

Chizhov, Alexander O. ;

Torgov, Vladimir I. ;

Kononov, Leonid O. .

SYNLETT, 2017, 28 (13) :1608-1613

[10] Novel Benzyl-Free Glycosyl Donors for Highly Stereoselective 1,2-cis-Fucosylation [J].

Abronina, Polina I. ;

Zinin, Alexander I. ;

Romashin, Denis A. ;

Malysheva, Nelly N. ;

Chizhov, Alexander O. ;

Kononov, Leonid O. .

SYNLETT, 2015, 26 (16) :2267-2271

← 1 2 3 4 →