Studies toward the site specific incorporation of sugars into proteins: Synthesis of glycosylated aminoacyl-tRNAs

Nour Eddine Fahmi; Serguei Golovine; Bixun Wang; Sidney M. Hecht

doi:10.1016/S0008-6215(00)00289-5

Studies toward the site specific incorporation of sugars into proteins: Synthesis of glycosylated aminoacyl-tRNAs

Nour Eddine Fahmi, Serguei Golovine, Bixun Wang, Sidney M. Hecht

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

17 Scopus citations

Abstract

A series of glycosylated serine derivatives was synthesized from peracetylated sugars and Fmoc-protected serine; these were chemically esterified with the tris-(tetrabutylammonium) salt of pdCpA. The fully protected and deprotected glycosylated aminoacyl pdCpAs were ligated enzymatically to an abbreviated tRNA (tRNA-C_OH) to provide the title compounds that are key intermediates in the elaboration of glycoproteins using readthrough of a nonsense codon.

Original language	English (US)
Pages (from-to)	149-164
Number of pages	16
Journal	Carbohydrate Research
Volume	330
Issue number	2
DOIs	https://doi.org/10.1016/S0008-6215(00)00289-5
State	Published - Jan 30 2001
Externally published	Yes

Keywords

Glycoprotein
Monosaccharide
S-serine
Site-specific glycosylation
Transfer RNA

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

Access to Document

10.1016/S0008-6215(00)00289-5

Cite this

@article{a24fa8996eab4e37901793c944090e2b,

title = "Studies toward the site specific incorporation of sugars into proteins: Synthesis of glycosylated aminoacyl-tRNAs",

abstract = "A series of glycosylated serine derivatives was synthesized from peracetylated sugars and Fmoc-protected serine; these were chemically esterified with the tris-(tetrabutylammonium) salt of pdCpA. The fully protected and deprotected glycosylated aminoacyl pdCpAs were ligated enzymatically to an abbreviated tRNA (tRNA-COH) to provide the title compounds that are key intermediates in the elaboration of glycoproteins using readthrough of a nonsense codon.",

keywords = "Glycoprotein, Monosaccharide, S-serine, Site-specific glycosylation, Transfer RNA",

author = "Fahmi, {Nour Eddine} and Serguei Golovine and Bixun Wang and Hecht, {Sidney M.}",

note = "Funding Information: We thank Dr M. Lodder for helpful discussions and Dr S. Mamaev for providing the plasmid used in this study. This work was supported by Research Grant CA77359, awarded by the National Cancer Institute. ",

year = "2001",

month = jan,

day = "30",

doi = "10.1016/S0008-6215(00)00289-5",

language = "English (US)",

volume = "330",

pages = "149--164",

journal = "Carbohydrate Research",

issn = "0008-6215",

publisher = "Elsevier BV",

number = "2",

}

TY - JOUR

T1 - Studies toward the site specific incorporation of sugars into proteins

T2 - Synthesis of glycosylated aminoacyl-tRNAs

AU - Fahmi, Nour Eddine

AU - Golovine, Serguei

AU - Wang, Bixun

AU - Hecht, Sidney M.

N1 - Funding Information: We thank Dr M. Lodder for helpful discussions and Dr S. Mamaev for providing the plasmid used in this study. This work was supported by Research Grant CA77359, awarded by the National Cancer Institute.

PY - 2001/1/30

Y1 - 2001/1/30

N2 - A series of glycosylated serine derivatives was synthesized from peracetylated sugars and Fmoc-protected serine; these were chemically esterified with the tris-(tetrabutylammonium) salt of pdCpA. The fully protected and deprotected glycosylated aminoacyl pdCpAs were ligated enzymatically to an abbreviated tRNA (tRNA-COH) to provide the title compounds that are key intermediates in the elaboration of glycoproteins using readthrough of a nonsense codon.

AB - A series of glycosylated serine derivatives was synthesized from peracetylated sugars and Fmoc-protected serine; these were chemically esterified with the tris-(tetrabutylammonium) salt of pdCpA. The fully protected and deprotected glycosylated aminoacyl pdCpAs were ligated enzymatically to an abbreviated tRNA (tRNA-COH) to provide the title compounds that are key intermediates in the elaboration of glycoproteins using readthrough of a nonsense codon.

KW - Glycoprotein

KW - Monosaccharide

KW - S-serine

KW - Site-specific glycosylation

KW - Transfer RNA

UR - http://www.scopus.com/inward/record.url?scp=0035969932&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035969932&partnerID=8YFLogxK

U2 - 10.1016/S0008-6215(00)00289-5

DO - 10.1016/S0008-6215(00)00289-5

M3 - Article

C2 - 11217968

AN - SCOPUS:0035969932

SN - 0008-6215

VL - 330

SP - 149

EP - 164

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 2

ER -

Studies toward the site specific incorporation of sugars into proteins: Synthesis of glycosylated aminoacyl-tRNAs

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this