Fluorescein-conjugated lysine monomers for solid phase synthesis of fluorescent peptides and PNA oligomers

J Lohse; N Harrit; O Dahl; Peter E. Nielsen

doi:10.1021/bc9700704

Fluorescein-conjugated lysine monomers for solid phase synthesis of fluorescent peptides and PNA oligomers

J Lohse, N Harrit, O Dahl, Peter E. Nielsen

Abstract

Fluorescein ethyl ester, I, was used to prepare the fluorescent mixed ester/ether 6-O-(carboxymethyl)-fluorescein ethyl ester, III. Conjugation of III to the epsilon-amino group of alpha-N-Boc-L-lysine, via the N-hydroxysuccinimde ester, IV, gave the Boc-protected fluorescein-conjugated lysine monomer V. Removal of the Boc group, followed by reaction with Fmoc chloride, gave the Fmoc-protected monomer, VI (Figure 1). These Boc- and Fmoc-protected fluorescein-conjugated lysines were readily incorporated into peptides and PNA oligomers during solid phase synthesis to give fluorescent products. Mass spectroscopy and UV studies showed that the fluorophore remains unchanged during solid phase synthesis. In contrast to fluorescein, the photophysical properties of these derivatives are pH independent from pH 3 to 8, with a molar absorption coefficient, epsilon max 456, of 2.9 x 10(4) M-1 cm-1 and fluorescence quantum yield, phi f, of 0.18.

Originalsprog	Engelsk
Tidsskrift	Bioconjugate Chemistry
Vol/bind	8
Udgave nummer	4
Sider (fra-til)	503-9
Antal sider	7
ISSN	1043-1802
DOI	https://doi.org/10.1021/bc9700704
Status	Udgivet - 1 jul. 1997

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10.1021/bc9700704

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title = "Fluorescein-conjugated lysine monomers for solid phase synthesis of fluorescent peptides and PNA oligomers",

abstract = "Fluorescein ethyl ester, I, was used to prepare the fluorescent mixed ester/ether 6-O-(carboxymethyl)-fluorescein ethyl ester, III. Conjugation of III to the epsilon-amino group of alpha-N-Boc-L-lysine, via the N-hydroxysuccinimde ester, IV, gave the Boc-protected fluorescein-conjugated lysine monomer V. Removal of the Boc group, followed by reaction with Fmoc chloride, gave the Fmoc-protected monomer, VI (Figure 1). These Boc- and Fmoc-protected fluorescein-conjugated lysines were readily incorporated into peptides and PNA oligomers during solid phase synthesis to give fluorescent products. Mass spectroscopy and UV studies showed that the fluorophore remains unchanged during solid phase synthesis. In contrast to fluorescein, the photophysical properties of these derivatives are pH independent from pH 3 to 8, with a molar absorption coefficient, epsilon max 456, of 2.9 x 10(4) M-1 cm-1 and fluorescence quantum yield, phi f, of 0.18.",

keywords = "Biopolymers, Chromatography, High Pressure Liquid, Fluorescein, Fluoresceins/chemistry, Lysine/chemistry, Mass Spectrometry/methods, Nucleic Acids/chemical synthesis, Peptides/chemical synthesis, Spectrophotometry, Ultraviolet",

author = "J Lohse and N Harrit and O Dahl and Nielsen, {Peter E.}",

year = "1997",

month = jul,

day = "1",

doi = "10.1021/bc9700704",

language = "English",

volume = "8",

pages = "503--9",

journal = "Bioconjugate Chemistry",

issn = "1043-1802",

publisher = "American Chemical Society",

number = "4",

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TY - JOUR

T1 - Fluorescein-conjugated lysine monomers for solid phase synthesis of fluorescent peptides and PNA oligomers

AU - Lohse, J

AU - Harrit, N

AU - Dahl, O

AU - Nielsen, Peter E.

PY - 1997/7/1

Y1 - 1997/7/1

N2 - Fluorescein ethyl ester, I, was used to prepare the fluorescent mixed ester/ether 6-O-(carboxymethyl)-fluorescein ethyl ester, III. Conjugation of III to the epsilon-amino group of alpha-N-Boc-L-lysine, via the N-hydroxysuccinimde ester, IV, gave the Boc-protected fluorescein-conjugated lysine monomer V. Removal of the Boc group, followed by reaction with Fmoc chloride, gave the Fmoc-protected monomer, VI (Figure 1). These Boc- and Fmoc-protected fluorescein-conjugated lysines were readily incorporated into peptides and PNA oligomers during solid phase synthesis to give fluorescent products. Mass spectroscopy and UV studies showed that the fluorophore remains unchanged during solid phase synthesis. In contrast to fluorescein, the photophysical properties of these derivatives are pH independent from pH 3 to 8, with a molar absorption coefficient, epsilon max 456, of 2.9 x 10(4) M-1 cm-1 and fluorescence quantum yield, phi f, of 0.18.

AB - Fluorescein ethyl ester, I, was used to prepare the fluorescent mixed ester/ether 6-O-(carboxymethyl)-fluorescein ethyl ester, III. Conjugation of III to the epsilon-amino group of alpha-N-Boc-L-lysine, via the N-hydroxysuccinimde ester, IV, gave the Boc-protected fluorescein-conjugated lysine monomer V. Removal of the Boc group, followed by reaction with Fmoc chloride, gave the Fmoc-protected monomer, VI (Figure 1). These Boc- and Fmoc-protected fluorescein-conjugated lysines were readily incorporated into peptides and PNA oligomers during solid phase synthesis to give fluorescent products. Mass spectroscopy and UV studies showed that the fluorophore remains unchanged during solid phase synthesis. In contrast to fluorescein, the photophysical properties of these derivatives are pH independent from pH 3 to 8, with a molar absorption coefficient, epsilon max 456, of 2.9 x 10(4) M-1 cm-1 and fluorescence quantum yield, phi f, of 0.18.

KW - Biopolymers

KW - Chromatography, High Pressure Liquid

KW - Fluorescein

KW - Fluoresceins/chemistry

KW - Lysine/chemistry

KW - Mass Spectrometry/methods

KW - Nucleic Acids/chemical synthesis

KW - Peptides/chemical synthesis

KW - Spectrophotometry, Ultraviolet

U2 - 10.1021/bc9700704

DO - 10.1021/bc9700704

M3 - Journal article

C2 - 9258448

SN - 1043-1802

VL - 8

SP - 503

EP - 509

JO - Bioconjugate Chemistry

JF - Bioconjugate Chemistry

IS - 4

ER -

Fluorescein-conjugated lysine monomers for solid phase synthesis of fluorescent peptides and PNA oligomers

Abstract

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