Synthesis of pdCpAs and transfer RNAs activated with thiothreonine and derivatives

Shengxi Chen; Nour Eddine Fahmi; Ryan C Nangreave; Youcef Mehellou; Sidney M Hecht

doi:10.1016/j.bmc.2012.02.024

Synthesis of pdCpAs and transfer RNAs activated with thiothreonine and derivatives

Shengxi Chen, Nour Eddine Fahmi, Ryan C Nangreave, Youcef Mehellou, Sidney M Hecht

Birmingham Medical School

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

7 Citations (Scopus)

Abstract

N,S-diprotected L-thiothreonine and L-allo-thiothreonine derivatives were synthesized using a novel chemical strategy, and used for esterification of the dinucleotide pdCpA. The aminoacylated dinucleotides were then employed for the preparation of activated suppressor tRNA(CUA) transcripts. Thiothreonine and allo-thiothreonine were incorporated into a predetermined position of a catalytically competent dihydrofolate reductase (DHFR) analogue lacking cysteine, and the elaborated proteins were derivatized site-specifically at the thiothreonine residue with a fluorophore.

Original language	English
Pages (from-to)	2679-89
Number of pages	11
Journal	Bioorganic & Medicinal Chemistry
Volume	20
Issue number	8
DOIs	https://doi.org/10.1016/j.bmc.2012.02.024
Publication status	Published - 15 Apr 2012

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title = "Synthesis of pdCpAs and transfer RNAs activated with thiothreonine and derivatives",

abstract = "N,S-diprotected L-thiothreonine and L-allo-thiothreonine derivatives were synthesized using a novel chemical strategy, and used for esterification of the dinucleotide pdCpA. The aminoacylated dinucleotides were then employed for the preparation of activated suppressor tRNA(CUA) transcripts. Thiothreonine and allo-thiothreonine were incorporated into a predetermined position of a catalytically competent dihydrofolate reductase (DHFR) analogue lacking cysteine, and the elaborated proteins were derivatized site-specifically at the thiothreonine residue with a fluorophore.",

author = "Shengxi Chen and Fahmi, {Nour Eddine} and Nangreave, {Ryan C} and Youcef Mehellou and Hecht, {Sidney M}",

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doi = "10.1016/j.bmc.2012.02.024",

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AU - Chen, Shengxi

AU - Fahmi, Nour Eddine

AU - Nangreave, Ryan C

AU - Mehellou, Youcef

AU - Hecht, Sidney M

PY - 2012/4/15

Y1 - 2012/4/15

N2 - N,S-diprotected L-thiothreonine and L-allo-thiothreonine derivatives were synthesized using a novel chemical strategy, and used for esterification of the dinucleotide pdCpA. The aminoacylated dinucleotides were then employed for the preparation of activated suppressor tRNA(CUA) transcripts. Thiothreonine and allo-thiothreonine were incorporated into a predetermined position of a catalytically competent dihydrofolate reductase (DHFR) analogue lacking cysteine, and the elaborated proteins were derivatized site-specifically at the thiothreonine residue with a fluorophore.

AB - N,S-diprotected L-thiothreonine and L-allo-thiothreonine derivatives were synthesized using a novel chemical strategy, and used for esterification of the dinucleotide pdCpA. The aminoacylated dinucleotides were then employed for the preparation of activated suppressor tRNA(CUA) transcripts. Thiothreonine and allo-thiothreonine were incorporated into a predetermined position of a catalytically competent dihydrofolate reductase (DHFR) analogue lacking cysteine, and the elaborated proteins were derivatized site-specifically at the thiothreonine residue with a fluorophore.

U2 - 10.1016/j.bmc.2012.02.024

DO - 10.1016/j.bmc.2012.02.024

M3 - Article

C2 - 22405920

VL - 20

SP - 2679

EP - 2689

JO - Bioorganic & Medicinal Chemistry

JF - Bioorganic & Medicinal Chemistry

IS - 8

ER -

Synthesis of pdCpAs and transfer RNAs activated with thiothreonine and derivatives

Abstract

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