Tetrahedron Letters

, volume 33 , issue 49 , pages 7605-7608

Application of t-butyldimethylsilyl ethers of serine, threonine and tyrosine in peptide syntheshsis

Peter Fischer ¹

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Nycomed Bioreg AS, Gaustadalléen 21, N-0371 Oslo, Norway |

Publication type: Journal Article

Publication date: 1992-01-01

Elsevier

Tetrahedron Letters

scimago Q3

wos Q3

SJR: 0.334

CiteScore: 3.2

Impact factor: 1.5

ISSN: 00404039, 18733581

DOI: 10.1016/s0040-4039(00)60836-5

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Organic Chemistry

Drug Discovery

Biochemistry

Abstract

The utility of Tbdms ( t -butyldimethylsilyl) ethers, prepared conveniently in a one-pot procedure from N α -Fmoc (9-fluorenylmethoxycarbonyl) and N α -Z (benzyloxycarbonyl) hydroxyamino acids, is demonstrated: peptide bond formation and esterification to 4-alkoxybenzylalcohol resin are achieved readily with these derivatives. The lability of the Tbdms ethers to various reagents enables selective deprotection of the hydroxyl side-chains after peptide chain assembly, desirable, e.g. , for phosphorylation or glycosilation. The t -butyldimethylsilyl ether protecting group can be introduced easily into hydroxyamino acids. It is compatible with solid phase peptide synthesis based on the N α -Fmoc group and can be removed selectively by judicious choice of deprotection conditions.

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Fischer P. Application of t-butyldimethylsilyl ethers of serine, threonine and tyrosine in peptide syntheshsis // Tetrahedron Letters. 1992. Vol. 33. No. 49. pp. 7605-7608.

GOST all authors (up to 50) Copy

Fischer P. Application of t-butyldimethylsilyl ethers of serine, threonine and tyrosine in peptide syntheshsis // Tetrahedron Letters. 1992. Vol. 33. No. 49. pp. 7605-7608.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1016/s0040-4039(00)60836-5

UR - https://doi.org/10.1016/s0040-4039(00)60836-5

TI - Application of t-butyldimethylsilyl ethers of serine, threonine and tyrosine in peptide syntheshsis

T2 - Tetrahedron Letters

AU - Fischer, Peter

PY - 1992

DA - 1992/01/01

PB - Elsevier

SP - 7605-7608

IS - 49

VL - 33

SN - 0040-4039

SN - 1873-3581

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{1992_Fischer,

author = {Peter Fischer},

title = {Application of t-butyldimethylsilyl ethers of serine, threonine and tyrosine in peptide syntheshsis},

journal = {Tetrahedron Letters},

year = {1992},

volume = {33},

publisher = {Elsevier},

month = {jan},

url = {https://doi.org/10.1016/s0040-4039(00)60836-5},

number = {49},

pages = {7605--7608},

doi = {10.1016/s0040-4039(00)60836-5}

}

MLA

Cite this

MLA Copy

Fischer, Peter. “Application of t-butyldimethylsilyl ethers of serine, threonine and tyrosine in peptide syntheshsis.” Tetrahedron Letters, vol. 33, no. 49, Jan. 1992, pp. 7605-7608. https://doi.org/10.1016/s0040-4039(00)60836-5.

Publisher

Elsevier

Journal

Tetrahedron Letters

scimago Q3

wos Q3

SJR

0.334

CiteScore

3.2

Impact factor

1.5

ISSN

00404039 (Print)

18733581 (Electronic)