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Evaluation of coupling conditions for the incorporation of N α-Fmoc-Tyr(PO3H2)-OH in solid-phase peptide synthesis

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Summary

In order to minimise the formation of the pyrophosphate derivative of the target peptide when side-chain-unprotected phopshotyrosine is used in solid-phase peptide synthesis, this building block can be incorporated using benzotriazolyloxy-tris-(dimethylamino)phosphonium hexafluorophosphate/1-hydroxybenzotriazole/N-methylmorpholine (1:1:2.3) in the presence of a chaotropic salt (0.4 M LiCl in N-methyl-2-pyrrolidinone).

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Abbreviations

BOP:

benzotriazolyloxy-tris-(dimethylamino)phosphonium hexafluorophosphate

DIEA:

diisopropylethylamine

Fmoc:

9-fluorenylmethoxycarbony

HATU:

N-[(dimethylamino)1H-1,2,3-triazolo[4,5-b]pyridin-1-ylmethylene]-N-methylmethan-aminium hexafluorophosphate N-oxide

HOBt:

1-hydroxybenzotriazole

HPLC:

high-performance liquid chromatography

MALDI-TOF:

matrix-assisted laser-desorption ionization time-of-flight mass spectrometry

NMM:

N-methylmorpholine

NMP:

N-methyl-2-pyrrolidinone

Pmc:

2,2,5,7,8-pentamethyl-chroman-6-sulfonyl

®:

solid support

TFA:

trifluoroacetic acid

TPTU:

2-(2-pyridon-1-yl)-1,1,3,3-tetramethyluroniumfluoroborate. Abbreviations used for amino acids follow the recommendations of the IUPAC-IUB Commission of Biochemical Nomenclature [Eur. J. Biochem., 138 (1984) 9]

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Authors and Affiliations

  1. Pharmaceuticals Division, Ciba-Geigy Ltd., CH-4002, Basel, Switzerland

    Carlos García-Echeverría

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  1. Carlos García-Echeverría
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García-Echeverría, C. Evaluation of coupling conditions for the incorporation of N α-Fmoc-Tyr(PO3H2)-OH in solid-phase peptide synthesis. Lett Pept Sci 2, 369–373 (1996). https://doi.org/10.1007/BF00120001

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  • DOI: https://doi.org/10.1007/BF00120001

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