Chemical synthesis of Ser/Thr AMPylated peptides

Rwaida A. Al-Eryani; Yan Li; Haydn L. Ball

doi:10.1016/j.tetlet.2010.01.097

Chemical synthesis of Ser/Thr AMPylated peptides

Rwaida A. Al-Eryani, Yan Li, Haydn L. Ball

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

9 Scopus citations

Abstract

A method for the solid phase chemical synthesis of AMPylated Ser/Thr containing peptides is described. Peptides were phosphonylated using the H-phosphonate method, then the adenosine moiety was introduced using 2′,3′-isopropylidene adenosine and the condensing reagent PyBOP. Oxidation with iodine yielded the desired AMPylated product in good yield following acidolytic cleavage from the resin support.

Original language	English (US)
Pages (from-to)	1730-1731
Number of pages	2
Journal	Tetrahedron Letters
Volume	51
Issue number	13
DOIs	https://doi.org/10.1016/j.tetlet.2010.01.097
State	Published - Mar 31 2010

Keywords

2′,3′-Isopropylidene adenosine
AMP
AMPylation
Benzotriazole-1-yl oxy-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBOP)
Bis(diethylamino) chlorophosphine
H-Phosphonate
SPPS

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2010.01.097

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title = "Chemical synthesis of Ser/Thr AMPylated peptides",

abstract = "A method for the solid phase chemical synthesis of AMPylated Ser/Thr containing peptides is described. Peptides were phosphonylated using the H-phosphonate method, then the adenosine moiety was introduced using 2′,3′-isopropylidene adenosine and the condensing reagent PyBOP. Oxidation with iodine yielded the desired AMPylated product in good yield following acidolytic cleavage from the resin support.",

keywords = "2′,3′-Isopropylidene adenosine, AMP, AMPylation, Benzotriazole-1-yl oxy-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBOP), Bis(diethylamino) chlorophosphine, H-Phosphonate, SPPS",

author = "Al-Eryani, {Rwaida A.} and Yan Li and Ball, {Haydn L.}",

year = "2010",

month = mar,

day = "31",

doi = "10.1016/j.tetlet.2010.01.097",

language = "English (US)",

volume = "51",

pages = "1730--1731",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Chemical synthesis of Ser/Thr AMPylated peptides

AU - Al-Eryani, Rwaida A.

AU - Li, Yan

AU - Ball, Haydn L.

PY - 2010/3/31

Y1 - 2010/3/31

N2 - A method for the solid phase chemical synthesis of AMPylated Ser/Thr containing peptides is described. Peptides were phosphonylated using the H-phosphonate method, then the adenosine moiety was introduced using 2′,3′-isopropylidene adenosine and the condensing reagent PyBOP. Oxidation with iodine yielded the desired AMPylated product in good yield following acidolytic cleavage from the resin support.

AB - A method for the solid phase chemical synthesis of AMPylated Ser/Thr containing peptides is described. Peptides were phosphonylated using the H-phosphonate method, then the adenosine moiety was introduced using 2′,3′-isopropylidene adenosine and the condensing reagent PyBOP. Oxidation with iodine yielded the desired AMPylated product in good yield following acidolytic cleavage from the resin support.

KW - 2′,3′-Isopropylidene adenosine

KW - AMP

KW - AMPylation

KW - Benzotriazole-1-yl oxy-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBOP)

KW - Bis(diethylamino) chlorophosphine

KW - H-Phosphonate

KW - SPPS

UR - http://www.scopus.com/inward/record.url?scp=76949084246&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=76949084246&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2010.01.097

DO - 10.1016/j.tetlet.2010.01.097

M3 - Article

AN - SCOPUS:76949084246

SN - 0040-4039

VL - 51

SP - 1730

EP - 1731

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 13

ER -

Chemical synthesis of Ser/Thr AMPylated peptides

Abstract

Keywords

ASJC Scopus subject areas

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