A facile strategy to prevent trifluoroacetylation of N-terminal proline peptides

C. Haase; M.F. Burton; S.M. Agten; L. Brunsveld

doi:10.1016/j.tetlet.2012.06.130

A facile strategy to prevent trifluoroacetylation of N-terminal proline peptides

C. Haase, M.F. Burton, S.M. Agten, L. Brunsveld

Chemical Biology

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Abstract

Unwanted trifluoroacetylation occurred at the N-terminus of prolinyl peptides during detachment from the solid phase. This was observed when the N-a-Fmoc protecting group had been removed prior to the final TFA treatment. Subtly changing the SPPS protocol and incorporating Boc- in place of the Fmoc-protected proline as the N-terminal building block efficiently suppressed this side reaction.

Original language	English
Pages (from-to)	4763-4765
Journal	Tetrahedron Letters
Volume	53
Issue number	35
DOIs	https://doi.org/10.1016/j.tetlet.2012.06.130
Publication status	Published - 2012

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10.1016/j.tetlet.2012.06.130

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title = "A facile strategy to prevent trifluoroacetylation of N-terminal proline peptides",

abstract = "Unwanted trifluoroacetylation occurred at the N-terminus of prolinyl peptides during detachment from the solid phase. This was observed when the N-a-Fmoc protecting group had been removed prior to the final TFA treatment. Subtly changing the SPPS protocol and incorporating Boc- in place of the Fmoc-protected proline as the N-terminal building block efficiently suppressed this side reaction.",

author = "C. Haase and M.F. Burton and S.M. Agten and L. Brunsveld",

year = "2012",

doi = "10.1016/j.tetlet.2012.06.130",

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T1 - A facile strategy to prevent trifluoroacetylation of N-terminal proline peptides

AU - Haase, C.

AU - Burton, M.F.

AU - Agten, S.M.

AU - Brunsveld, L.

PY - 2012

Y1 - 2012

N2 - Unwanted trifluoroacetylation occurred at the N-terminus of prolinyl peptides during detachment from the solid phase. This was observed when the N-a-Fmoc protecting group had been removed prior to the final TFA treatment. Subtly changing the SPPS protocol and incorporating Boc- in place of the Fmoc-protected proline as the N-terminal building block efficiently suppressed this side reaction.

AB - Unwanted trifluoroacetylation occurred at the N-terminus of prolinyl peptides during detachment from the solid phase. This was observed when the N-a-Fmoc protecting group had been removed prior to the final TFA treatment. Subtly changing the SPPS protocol and incorporating Boc- in place of the Fmoc-protected proline as the N-terminal building block efficiently suppressed this side reaction.

U2 - 10.1016/j.tetlet.2012.06.130

DO - 10.1016/j.tetlet.2012.06.130

M3 - Article

SN - 0040-4039

VL - 53

SP - 4763

EP - 4765

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 35

ER -

A facile strategy to prevent trifluoroacetylation of N-terminal proline peptides

Abstract

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