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Reductive alkylation of proteins using iridium catalyzed transfer hydrogenation
被引:132
作者
:
McFarland, JM
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
McFarland, JM
Francis, MB
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
Francis, MB
[
1
]
机构
:
[1]
Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
[2]
Univ Calif Berkeley, Lawrence Berkeley Lab, Div Mat Sci, Berkeley, CA 94720 USA
来源
:
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
|
2005年
/ 127卷
/ 39期
关键词
:
D O I
:
10.1021/ja054686c
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
An efficient transition metal catalyzed procedure for the reductive alkylation of proteins has been developed. Imines formed from the condensation of aldehydes (1 mM) with lysine residues and the N-terminus can be reduced efficiently by a [Cp*Ir(4,4′-dimethoxy-2,2′-bipyridine)(H2O)]SO4 catalyst in the presence of formate ions. The reaction proceeds readily at pH 7.4 in aqueous phosphate buffer at temperatures ranging from 22 to 37 °C, and reaches high levels of conversion for a number of aromatic aldehydes. UV experiments have confirmed that the catalyst does not bind to protein substrates. The utility of the reaction has been demonstrated through an efficient two-step procedure for the attachment of unfunctionalized poly(ethylene glycol) to protein targets. Copyright © 2005 American Chemical Society.
引用
收藏
页码:13490 / 13491
页数:2
相关论文
共 16 条
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Isolation and crystal structure of a water-soluble iridium hydride: A robust and highly active catalyst for acid-catalyzed transfer hydrogenations of carbonyl compounds in acidic media
Abura, T
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0
引用数:
0
h-index:
0
机构:
Osaka Univ, PRESTO, Grad Sch Engn, Dept Mat & Life Sci, Suita, Osaka 5650871, Japan
Abura, T
Ogo, S
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0
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Osaka Univ, PRESTO, Grad Sch Engn, Dept Mat & Life Sci, Suita, Osaka 5650871, Japan
Ogo, S
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h-index:
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Watanabe, Y
Fukuzumi, S
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0
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0
h-index:
0
机构:
Osaka Univ, PRESTO, Grad Sch Engn, Dept Mat & Life Sci, Suita, Osaka 5650871, Japan
Fukuzumi, S
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
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125
(14)
: 4149
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4154
[2]
Selective tryptophan modification with rhodium carbenoids in aqueous solution
Antos, JM
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0
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0
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Lawrence Berkeley Natl Labs, Div Mat Sci, Berkeley, CA 94720 USA
Antos, JM
Francis, MB
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0
引用数:
0
h-index:
0
机构:
Lawrence Berkeley Natl Labs, Div Mat Sci, Berkeley, CA 94720 USA
Lawrence Berkeley Natl Labs, Div Mat Sci, Berkeley, CA 94720 USA
Francis, MB
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2004,
126
(33)
: 10256
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10257
[3]
Chemoselective Pd(0)-catalyzed peptide coupling in water
Bong, DT
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0
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0
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Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Bong, DT
Ghadiri, MR
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0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Ghadiri, MR
[J].
ORGANIC LETTERS,
2001,
3
(16)
: 2509
-
2511
[4]
Determining the geometries of transition states by use of antihydrophohic additives in water
Breslow, R
论文数:
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引用数:
0
h-index:
0
机构:
Columbia Univ, Dept Chem, New York, NY 10027 USA
Columbia Univ, Dept Chem, New York, NY 10027 USA
Breslow, R
[J].
ACCOUNTS OF CHEMICAL RESEARCH,
2004,
37
(07)
: 471
-
478
[5]
PI-ARENE AQUA COMPLEXES OF COBALT, RHODIUM, IRIDIUM, AND RUTHENIUM - PREPARATION, STRUCTURE, AND KINETICS OF WATER EXCHANGE AND WATER SUBSTITUTION
DADCI, L
论文数:
0
引用数:
0
h-index:
0
机构:
TH DARMSTADT,EDUARD ZINTL INST ANORGAN CHEM,D-64289 DARMSTADT,GERMANY
DADCI, L
ELIAS, H
论文数:
0
引用数:
0
h-index:
0
机构:
TH DARMSTADT,EDUARD ZINTL INST ANORGAN CHEM,D-64289 DARMSTADT,GERMANY
ELIAS, H
FREY, U
论文数:
0
引用数:
0
h-index:
0
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TH DARMSTADT,EDUARD ZINTL INST ANORGAN CHEM,D-64289 DARMSTADT,GERMANY
FREY, U
HORNIG, A
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0
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0
h-index:
0
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TH DARMSTADT,EDUARD ZINTL INST ANORGAN CHEM,D-64289 DARMSTADT,GERMANY
HORNIG, A
KOELLE, U
论文数:
0
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0
h-index:
0
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TH DARMSTADT,EDUARD ZINTL INST ANORGAN CHEM,D-64289 DARMSTADT,GERMANY
KOELLE, U
MERBACH, AE
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0
h-index:
0
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TH DARMSTADT,EDUARD ZINTL INST ANORGAN CHEM,D-64289 DARMSTADT,GERMANY
MERBACH, AE
PAULUS, H
论文数:
0
引用数:
0
h-index:
0
机构:
TH DARMSTADT,EDUARD ZINTL INST ANORGAN CHEM,D-64289 DARMSTADT,GERMANY
PAULUS, H
SCHNEIDER, JS
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0
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0
h-index:
0
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TH DARMSTADT,EDUARD ZINTL INST ANORGAN CHEM,D-64289 DARMSTADT,GERMANY
SCHNEIDER, JS
[J].
INORGANIC CHEMISTRY,
1995,
34
(01)
: 306
-
315
[6]
Dibowski H, 1998, ANGEW CHEM INT EDIT, V37, P476, DOI 10.1002/(SICI)1521-3773(19980302)37:4<476::AID-ANIE476>3.0.CO
[7]
2-2
[8]
Half-sandwich complexes with 4,7-dihydroxy-1,10-phenanthroline: Water-soluble, highly efficient catalysts for hydrogenation of bicarbonate attributable to the generation of an oxyanion on the catalyst ligand
Himeda, Y
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0
引用数:
0
h-index:
0
机构:
Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058565, Japan
Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058565, Japan
Himeda, Y
Onozawa-Komatsuzaki, N
论文数:
0
引用数:
0
h-index:
0
机构:
Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058565, Japan
Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058565, Japan
Onozawa-Komatsuzaki, N
Sugihara, H
论文数:
0
引用数:
0
h-index:
0
机构:
Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058565, Japan
Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058565, Japan
Sugihara, H
Arakawa, H
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0
h-index:
0
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Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058565, Japan
Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058565, Japan
Arakawa, H
Kasuga, K
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h-index:
0
机构:
Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058565, Japan
Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058565, Japan
Kasuga, K
[J].
ORGANOMETALLICS,
2004,
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(07)
: 1480
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1483
[9]
A three-component Mannich-type reaction for selective tyrosine bioconjugation
Joshi, NS
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Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
Joshi, NS
Whitaker, LR
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Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
Whitaker, LR
Francis, MB
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h-index:
0
机构:
Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
Francis, MB
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2004,
126
(49)
: 15942
-
15943
[10]
pH-selective synthesis and structures of alkynyl, acyl, and ketonyl intermediates in anti-Markovnikov and Markovnikov hydrations of a terminal alkyne with a water-soluble iridium aqua complex in water
Ogo, S
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0
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0
h-index:
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Osaka Univ, Grad Sch Engn, Dept Mat & Life Sci, PRESTO, Suita, Osaka 5650871, Japan
Ogo, S
Uehara, K
论文数:
0
引用数:
0
h-index:
0
机构:
Osaka Univ, Grad Sch Engn, Dept Mat & Life Sci, PRESTO, Suita, Osaka 5650871, Japan
Uehara, K
Abura, T
论文数:
0
引用数:
0
h-index:
0
机构:
Osaka Univ, Grad Sch Engn, Dept Mat & Life Sci, PRESTO, Suita, Osaka 5650871, Japan
Abura, T
论文数:
引用数:
h-index:
机构:
Watanabe, Y
Fukuzumi, S
论文数:
0
引用数:
0
h-index:
0
机构:
Osaka Univ, Grad Sch Engn, Dept Mat & Life Sci, PRESTO, Suita, Osaka 5650871, Japan
Fukuzumi, S
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2004,
126
(50)
: 16520
-
16527
←
1
2
→
共 16 条
[1]
Isolation and crystal structure of a water-soluble iridium hydride: A robust and highly active catalyst for acid-catalyzed transfer hydrogenations of carbonyl compounds in acidic media
Abura, T
论文数:
0
引用数:
0
h-index:
0
机构:
Osaka Univ, PRESTO, Grad Sch Engn, Dept Mat & Life Sci, Suita, Osaka 5650871, Japan
Abura, T
Ogo, S
论文数:
0
引用数:
0
h-index:
0
机构:
Osaka Univ, PRESTO, Grad Sch Engn, Dept Mat & Life Sci, Suita, Osaka 5650871, Japan
Ogo, S
论文数:
引用数:
h-index:
机构:
Watanabe, Y
Fukuzumi, S
论文数:
0
引用数:
0
h-index:
0
机构:
Osaka Univ, PRESTO, Grad Sch Engn, Dept Mat & Life Sci, Suita, Osaka 5650871, Japan
Fukuzumi, S
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2003,
125
(14)
: 4149
-
4154
[2]
Selective tryptophan modification with rhodium carbenoids in aqueous solution
Antos, JM
论文数:
0
引用数:
0
h-index:
0
机构:
Lawrence Berkeley Natl Labs, Div Mat Sci, Berkeley, CA 94720 USA
Antos, JM
Francis, MB
论文数:
0
引用数:
0
h-index:
0
机构:
Lawrence Berkeley Natl Labs, Div Mat Sci, Berkeley, CA 94720 USA
Lawrence Berkeley Natl Labs, Div Mat Sci, Berkeley, CA 94720 USA
Francis, MB
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2004,
126
(33)
: 10256
-
10257
[3]
Chemoselective Pd(0)-catalyzed peptide coupling in water
Bong, DT
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Bong, DT
Ghadiri, MR
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
Ghadiri, MR
[J].
ORGANIC LETTERS,
2001,
3
(16)
: 2509
-
2511
[4]
Determining the geometries of transition states by use of antihydrophohic additives in water
Breslow, R
论文数:
0
引用数:
0
h-index:
0
机构:
Columbia Univ, Dept Chem, New York, NY 10027 USA
Columbia Univ, Dept Chem, New York, NY 10027 USA
Breslow, R
[J].
ACCOUNTS OF CHEMICAL RESEARCH,
2004,
37
(07)
: 471
-
478
[5]
PI-ARENE AQUA COMPLEXES OF COBALT, RHODIUM, IRIDIUM, AND RUTHENIUM - PREPARATION, STRUCTURE, AND KINETICS OF WATER EXCHANGE AND WATER SUBSTITUTION
DADCI, L
论文数:
0
引用数:
0
h-index:
0
机构:
TH DARMSTADT,EDUARD ZINTL INST ANORGAN CHEM,D-64289 DARMSTADT,GERMANY
DADCI, L
ELIAS, H
论文数:
0
引用数:
0
h-index:
0
机构:
TH DARMSTADT,EDUARD ZINTL INST ANORGAN CHEM,D-64289 DARMSTADT,GERMANY
ELIAS, H
FREY, U
论文数:
0
引用数:
0
h-index:
0
机构:
TH DARMSTADT,EDUARD ZINTL INST ANORGAN CHEM,D-64289 DARMSTADT,GERMANY
FREY, U
HORNIG, A
论文数:
0
引用数:
0
h-index:
0
机构:
TH DARMSTADT,EDUARD ZINTL INST ANORGAN CHEM,D-64289 DARMSTADT,GERMANY
HORNIG, A
KOELLE, U
论文数:
0
引用数:
0
h-index:
0
机构:
TH DARMSTADT,EDUARD ZINTL INST ANORGAN CHEM,D-64289 DARMSTADT,GERMANY
KOELLE, U
MERBACH, AE
论文数:
0
引用数:
0
h-index:
0
机构:
TH DARMSTADT,EDUARD ZINTL INST ANORGAN CHEM,D-64289 DARMSTADT,GERMANY
MERBACH, AE
PAULUS, H
论文数:
0
引用数:
0
h-index:
0
机构:
TH DARMSTADT,EDUARD ZINTL INST ANORGAN CHEM,D-64289 DARMSTADT,GERMANY
PAULUS, H
SCHNEIDER, JS
论文数:
0
引用数:
0
h-index:
0
机构:
TH DARMSTADT,EDUARD ZINTL INST ANORGAN CHEM,D-64289 DARMSTADT,GERMANY
SCHNEIDER, JS
[J].
INORGANIC CHEMISTRY,
1995,
34
(01)
: 306
-
315
[6]
Dibowski H, 1998, ANGEW CHEM INT EDIT, V37, P476, DOI 10.1002/(SICI)1521-3773(19980302)37:4<476::AID-ANIE476>3.0.CO
[7]
2-2
[8]
Half-sandwich complexes with 4,7-dihydroxy-1,10-phenanthroline: Water-soluble, highly efficient catalysts for hydrogenation of bicarbonate attributable to the generation of an oxyanion on the catalyst ligand
Himeda, Y
论文数:
0
引用数:
0
h-index:
0
机构:
Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058565, Japan
Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058565, Japan
Himeda, Y
Onozawa-Komatsuzaki, N
论文数:
0
引用数:
0
h-index:
0
机构:
Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058565, Japan
Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058565, Japan
Onozawa-Komatsuzaki, N
Sugihara, H
论文数:
0
引用数:
0
h-index:
0
机构:
Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058565, Japan
Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058565, Japan
Sugihara, H
Arakawa, H
论文数:
0
引用数:
0
h-index:
0
机构:
Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058565, Japan
Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058565, Japan
Arakawa, H
Kasuga, K
论文数:
0
引用数:
0
h-index:
0
机构:
Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058565, Japan
Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058565, Japan
Kasuga, K
[J].
ORGANOMETALLICS,
2004,
23
(07)
: 1480
-
1483
[9]
A three-component Mannich-type reaction for selective tyrosine bioconjugation
Joshi, NS
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
Joshi, NS
Whitaker, LR
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
Whitaker, LR
Francis, MB
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
Francis, MB
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2004,
126
(49)
: 15942
-
15943
[10]
pH-selective synthesis and structures of alkynyl, acyl, and ketonyl intermediates in anti-Markovnikov and Markovnikov hydrations of a terminal alkyne with a water-soluble iridium aqua complex in water
Ogo, S
论文数:
0
引用数:
0
h-index:
0
机构:
Osaka Univ, Grad Sch Engn, Dept Mat & Life Sci, PRESTO, Suita, Osaka 5650871, Japan
Ogo, S
Uehara, K
论文数:
0
引用数:
0
h-index:
0
机构:
Osaka Univ, Grad Sch Engn, Dept Mat & Life Sci, PRESTO, Suita, Osaka 5650871, Japan
Uehara, K
Abura, T
论文数:
0
引用数:
0
h-index:
0
机构:
Osaka Univ, Grad Sch Engn, Dept Mat & Life Sci, PRESTO, Suita, Osaka 5650871, Japan
Abura, T
论文数:
引用数:
h-index:
机构:
Watanabe, Y
Fukuzumi, S
论文数:
0
引用数:
0
h-index:
0
机构:
Osaka Univ, Grad Sch Engn, Dept Mat & Life Sci, PRESTO, Suita, Osaka 5650871, Japan
Fukuzumi, S
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2004,
126
(50)
: 16520
-
16527
←
1
2
→