The chemical synthesis of glycosylphosphatidylinositol anchors from Trypanosoma cruzi Trypomastigote mucins: exploration of ester and acetal type permanent protecting groups

Dmitry V. Yashunsky; Vladimir S. Borodkin; Philip G. McGivern; Michael A. J. Ferguson; Andrei V. Nikolaev

doi:10.1021/bk-2007-0960.ch016

The chemical synthesis of glycosylphosphatidylinositol anchors from Trypanosoma cruzi Trypomastigote mucins: exploration of ester and acetal type permanent protecting groups

Dmitry V. Yashunsky
, Vladimir S. Borodkin
, Philip G. McGivern
, Michael A. J. Ferguson
, Andrei V. Nikolaev

Research output: Chapter in Book/Report/Conference proceeding › Conference contribution

Abstract

The protozoan parasite Trypanosoma cruzi is a causative agent of Chagas' disease, which affects millions of people in South and Central America. Throughout the life cycle, T cruzi produce both common and stage-specific glycosylphosphatidylinositol(GPI)-anchored cell-surface macromolecules. The purified GPI fraction of T cruzi trypomastigote mucins (tGPI) revealed extraordinary pro-inflammatory activity (comparable to those of bacterial lipopolysaccharide), which was allegedly associated with the presence of unsaturated fatty acids in the lipid moiety (structures 1 and 2). Two distinct novel synthetic strategies, both implicating the use of non-benzyl type protecting groups, were designed and applied for the chemical preparation of the tGPIs 1 and 2.

Original language	English
Title of host publication	Frontiers in modern carbohydrate chemistry
Editors	A. V. Demchenko
Place of Publication	Washington
Publisher	American Chemical Society
Pages	285-306
Number of pages	22
ISBN (Electronic)	9780841220782
ISBN (Print)	9780841239708
DOIs	https://doi.org/10.1021/bk-2007-0960.ch016
Publication status	Published - 2007
Event	The 229th ACS National Meeting 2005: Symposium on Frontiers in Modern Carbohydrate Chemistry - San Diego, United States Duration: 13 Mar 2005 → 17 Mar 2005 http://oasys2.confex.com/acs/229nm/techprogram/

Publication series

Name	ACS Symposium series
Volume	960

Conference

Conference	The 229th ACS National Meeting 2005: Symposium on Frontiers in Modern Carbohydrate Chemistry
Country/Territory	United States
City	San Diego
Period	13/03/05 → 17/03/05
Internet address	http://oasys2.confex.com/acs/229nm/techprogram/

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

RAT-BRAIN THY-1
GPI-ANCHOR
MEMBRANE ANCHOR
BIOSYNTHESIS
GLYCOPROTEIN
DERIVATIVES
FRAGMENT
PARASITE
ANALOGS
BRUCEI

Access to Document

10.1021/bk-2007-0960.ch016

Cite this

Yashunsky, D. V., Borodkin, V. S., McGivern, P. G., Ferguson, M. A. J., & Nikolaev, A. V. (2007). The chemical synthesis of glycosylphosphatidylinositol anchors from Trypanosoma cruzi Trypomastigote mucins: exploration of ester and acetal type permanent protecting groups. In A. V. Demchenko (Ed.), Frontiers in modern carbohydrate chemistry (pp. 285-306). (ACS Symposium series; Vol. 960). American Chemical Society. https://doi.org/10.1021/bk-2007-0960.ch016

Yashunsky, Dmitry V. ; Borodkin, Vladimir S. ; McGivern, Philip G. et al. / The chemical synthesis of glycosylphosphatidylinositol anchors from Trypanosoma cruzi Trypomastigote mucins : exploration of ester and acetal type permanent protecting groups. Frontiers in modern carbohydrate chemistry . editor / A. V. Demchenko. Washington : American Chemical Society, 2007. pp. 285-306 (ACS Symposium series).

@inproceedings{21b325f7dc264975a96cc86c1595caa4,

title = "The chemical synthesis of glycosylphosphatidylinositol anchors from Trypanosoma cruzi Trypomastigote mucins: exploration of ester and acetal type permanent protecting groups",

abstract = "The protozoan parasite Trypanosoma cruzi is a causative agent of Chagas' disease, which affects millions of people in South and Central America. Throughout the life cycle, T cruzi produce both common and stage-specific glycosylphosphatidylinositol(GPI)-anchored cell-surface macromolecules. The purified GPI fraction of T cruzi trypomastigote mucins (tGPI) revealed extraordinary pro-inflammatory activity (comparable to those of bacterial lipopolysaccharide), which was allegedly associated with the presence of unsaturated fatty acids in the lipid moiety (structures 1 and 2). Two distinct novel synthetic strategies, both implicating the use of non-benzyl type protecting groups, were designed and applied for the chemical preparation of the tGPIs 1 and 2.",

keywords = "RAT-BRAIN THY-1, GPI-ANCHOR, MEMBRANE ANCHOR, BIOSYNTHESIS, GLYCOPROTEIN, DERIVATIVES, FRAGMENT, PARASITE, ANALOGS, BRUCEI",

author = "Yashunsky, \{Dmitry V.\} and Borodkin, \{Vladimir S.\} and McGivern, \{Philip G.\} and Ferguson, \{Michael A. J.\} and Nikolaev, \{Andrei V.\}",

year = "2007",

doi = "10.1021/bk-2007-0960.ch016",

language = "English",

isbn = "9780841239708",

series = "ACS Symposium series",

publisher = "American Chemical Society",

pages = "285--306",

editor = "Demchenko, \{A. V.\}",

booktitle = "Frontiers in modern carbohydrate chemistry",

address = "United States",

note = "The 229th ACS National Meeting 2005: Symposium on Frontiers in Modern Carbohydrate Chemistry ; Conference date: 13-03-2005 Through 17-03-2005",

url = "http://oasys2.confex.com/acs/229nm/techprogram/",

}

Yashunsky, DV, Borodkin, VS, McGivern, PG, Ferguson, MAJ & Nikolaev, AV 2007, The chemical synthesis of glycosylphosphatidylinositol anchors from Trypanosoma cruzi Trypomastigote mucins: exploration of ester and acetal type permanent protecting groups. in AV Demchenko (ed.), Frontiers in modern carbohydrate chemistry . ACS Symposium series, vol. 960, American Chemical Society, Washington, pp. 285-306, The 229th ACS National Meeting 2005: Symposium on Frontiers in Modern Carbohydrate Chemistry, San Diego, United States, 13/03/05. https://doi.org/10.1021/bk-2007-0960.ch016

The chemical synthesis of glycosylphosphatidylinositol anchors from Trypanosoma cruzi Trypomastigote mucins: exploration of ester and acetal type permanent protecting groups. / Yashunsky, Dmitry V.; Borodkin, Vladimir S.; McGivern, Philip G. et al.
Frontiers in modern carbohydrate chemistry . ed. / A. V. Demchenko. Washington: American Chemical Society, 2007. p. 285-306 (ACS Symposium series; Vol. 960).

Research output: Chapter in Book/Report/Conference proceeding › Conference contribution

TY - GEN

T1 - The chemical synthesis of glycosylphosphatidylinositol anchors from Trypanosoma cruzi Trypomastigote mucins

T2 - The 229th ACS National Meeting 2005: Symposium on Frontiers in Modern Carbohydrate Chemistry

AU - Yashunsky, Dmitry V.

AU - Borodkin, Vladimir S.

AU - McGivern, Philip G.

AU - Ferguson, Michael A. J.

AU - Nikolaev, Andrei V.

PY - 2007

Y1 - 2007

N2 - The protozoan parasite Trypanosoma cruzi is a causative agent of Chagas' disease, which affects millions of people in South and Central America. Throughout the life cycle, T cruzi produce both common and stage-specific glycosylphosphatidylinositol(GPI)-anchored cell-surface macromolecules. The purified GPI fraction of T cruzi trypomastigote mucins (tGPI) revealed extraordinary pro-inflammatory activity (comparable to those of bacterial lipopolysaccharide), which was allegedly associated with the presence of unsaturated fatty acids in the lipid moiety (structures 1 and 2). Two distinct novel synthetic strategies, both implicating the use of non-benzyl type protecting groups, were designed and applied for the chemical preparation of the tGPIs 1 and 2.

AB - The protozoan parasite Trypanosoma cruzi is a causative agent of Chagas' disease, which affects millions of people in South and Central America. Throughout the life cycle, T cruzi produce both common and stage-specific glycosylphosphatidylinositol(GPI)-anchored cell-surface macromolecules. The purified GPI fraction of T cruzi trypomastigote mucins (tGPI) revealed extraordinary pro-inflammatory activity (comparable to those of bacterial lipopolysaccharide), which was allegedly associated with the presence of unsaturated fatty acids in the lipid moiety (structures 1 and 2). Two distinct novel synthetic strategies, both implicating the use of non-benzyl type protecting groups, were designed and applied for the chemical preparation of the tGPIs 1 and 2.

KW - RAT-BRAIN THY-1

KW - GPI-ANCHOR

KW - MEMBRANE ANCHOR

KW - BIOSYNTHESIS

KW - GLYCOPROTEIN

KW - DERIVATIVES

KW - FRAGMENT

KW - PARASITE

KW - ANALOGS

KW - BRUCEI

U2 - 10.1021/bk-2007-0960.ch016

DO - 10.1021/bk-2007-0960.ch016

M3 - Conference contribution

SN - 9780841239708

T3 - ACS Symposium series

SP - 285

EP - 306

BT - Frontiers in modern carbohydrate chemistry

A2 - Demchenko, A. V.

PB - American Chemical Society

CY - Washington

Y2 - 13 March 2005 through 17 March 2005

ER -

Yashunsky DV, Borodkin VS, McGivern PG, Ferguson MAJ, Nikolaev AV. The chemical synthesis of glycosylphosphatidylinositol anchors from Trypanosoma cruzi Trypomastigote mucins: exploration of ester and acetal type permanent protecting groups. In Demchenko AV, editor, Frontiers in modern carbohydrate chemistry . Washington: American Chemical Society. 2007. p. 285-306. (ACS Symposium series). doi: 10.1021/bk-2007-0960.ch016

The chemical synthesis of glycosylphosphatidylinositol anchors from Trypanosoma cruzi Trypomastigote mucins: exploration of ester and acetal type permanent protecting groups

Abstract

Publication series

Conference

UN SDGs

Keywords

Access to Document

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Cite this