共 43 条
Chemoenzymatic Synthesis of (S)-Hexafluoroleucine and (S)-Tetrafluoroleucine
被引:21
作者:

Chiu, Hsien-Po
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机构:
SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA

Cheng, Richard P.
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SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
机构:
[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
关键词:
D O I:
10.1021/ol702470j
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
We have developed a short chemoenzymatic synthesis for both (S)-5,5,5,5',5',5'-hexafluoroleucine (Hfl) and (S)-5,5,5',5'-tetrafluoroleucine (Qfl) on gram scale. Qfl was incorporated into a peptide using standard solid-phase peptide synthesis protocols to measure its helix propensity. The helix propensity for Qfl is 0.68 kcal center dot mol(-1) more favorable compared to Hfl.
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页码:5517 / 5520
页数:4
相关论文
共 43 条
[21]
Fluorine in a native protein environment -: How the spatial demand and polarity of fluoroalkyl groups affect protein folding
[J].
Jaeckel, Christian
;
Salwiczek, Mario
;
Koksch, Beate
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2006, 45 (25)
:4198-4203

Jaeckel, Christian
论文数: 0 引用数: 0
h-index: 0
机构:
Free Univ Berlin, Dept Chem & Biochem, D-14195 Berlin, Germany Free Univ Berlin, Dept Chem & Biochem, D-14195 Berlin, Germany

Salwiczek, Mario
论文数: 0 引用数: 0
h-index: 0
机构:
Free Univ Berlin, Dept Chem & Biochem, D-14195 Berlin, Germany Free Univ Berlin, Dept Chem & Biochem, D-14195 Berlin, Germany

Koksch, Beate
论文数: 0 引用数: 0
h-index: 0
机构:
Free Univ Berlin, Dept Chem & Biochem, D-14195 Berlin, Germany Free Univ Berlin, Dept Chem & Biochem, D-14195 Berlin, Germany
[22]
Enzymatic reduction of alpha-keto acids leading to L-amino acids, D- or L-hydroxy acids
[J].
Krix, G
;
Bommarius, AS
;
Drauz, K
;
Kottenhahn, M
;
Schwarm, M
;
Kula, MR
.
JOURNAL OF BIOTECHNOLOGY,
1997, 53 (01)
:29-39

Krix, G
论文数: 0 引用数: 0
h-index: 0
机构: UNIV DUSSELDORF,INST ENZYME TECHNOL,D-52404 JULICH,GERMANY

Bommarius, AS
论文数: 0 引用数: 0
h-index: 0
机构: UNIV DUSSELDORF,INST ENZYME TECHNOL,D-52404 JULICH,GERMANY

Drauz, K
论文数: 0 引用数: 0
h-index: 0
机构: UNIV DUSSELDORF,INST ENZYME TECHNOL,D-52404 JULICH,GERMANY

Kottenhahn, M
论文数: 0 引用数: 0
h-index: 0
机构: UNIV DUSSELDORF,INST ENZYME TECHNOL,D-52404 JULICH,GERMANY

Schwarm, M
论文数: 0 引用数: 0
h-index: 0
机构: UNIV DUSSELDORF,INST ENZYME TECHNOL,D-52404 JULICH,GERMANY

Kula, MR
论文数: 0 引用数: 0
h-index: 0
机构: UNIV DUSSELDORF,INST ENZYME TECHNOL,D-52404 JULICH,GERMANY
[23]
Modulating protein structure with fluorous amino acids: Increased stability and native-like structure conferred on a 4-helix bundle protein by hexafluoroleucine
[J].
Lee, HY
;
Lee, KH
;
Al-Hashimi, HM
;
Marsh, ENG
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2006, 128 (01)
:337-343

Lee, HY
论文数: 0 引用数: 0
h-index: 0
机构: Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

Lee, KH
论文数: 0 引用数: 0
h-index: 0
机构: Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

Al-Hashimi, HM
论文数: 0 引用数: 0
h-index: 0
机构: Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

Marsh, ENG
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
[24]
Fluorous effect in proteins:: De novo design and characterization of a four-α-helix bundle protein containing hexafluoroleucine
[J].
Lee, KH
;
Lee, HY
;
Slutsky, MM
;
Anderson, JT
;
Marsh, ENG
.
BIOCHEMISTRY,
2004, 43 (51)
:16277-16284

Lee, KH
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

Lee, HY
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

Slutsky, MM
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

Anderson, JT
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

Marsh, ENG
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
[25]
Interaction between water and polar groups of the helix backbone: An important determinant of helix propensities
[J].
Luo, PZ
;
Baldwin, RL
.
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA,
1999, 96 (09)
:4930-4935

Luo, PZ
论文数: 0 引用数: 0
h-index: 0
机构:
Stanford Univ, Beckman Ctr, Dept Biochem, Med Ctr, Stanford, CA 94305 USA Stanford Univ, Beckman Ctr, Dept Biochem, Med Ctr, Stanford, CA 94305 USA

Baldwin, RL
论文数: 0 引用数: 0
h-index: 0
机构:
Stanford Univ, Beckman Ctr, Dept Biochem, Med Ctr, Stanford, CA 94305 USA Stanford Univ, Beckman Ctr, Dept Biochem, Med Ctr, Stanford, CA 94305 USA
[26]
A designed P1 cysteine mimetic for covalent and non-covalent inhibitors of HCVNS3 protease
[J].
Narjes, F
;
Koehler, KF
;
Koch, U
;
Gerlach, B
;
Colarusso, S
;
Steinkuhler, C
;
Brunetti, M
;
Altamura, S
;
De Francesco, R
;
Matassa, VG
.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,
2002, 12 (04)
:701-704

Narjes, F
论文数: 0 引用数: 0
h-index: 0
机构: IRBM, MRL Rome, Dept Chem, I-00040 Rome, Italy

Koehler, KF
论文数: 0 引用数: 0
h-index: 0
机构: IRBM, MRL Rome, Dept Chem, I-00040 Rome, Italy

Koch, U
论文数: 0 引用数: 0
h-index: 0
机构: IRBM, MRL Rome, Dept Chem, I-00040 Rome, Italy

Gerlach, B
论文数: 0 引用数: 0
h-index: 0
机构: IRBM, MRL Rome, Dept Chem, I-00040 Rome, Italy

Colarusso, S
论文数: 0 引用数: 0
h-index: 0
机构: IRBM, MRL Rome, Dept Chem, I-00040 Rome, Italy

Steinkuhler, C
论文数: 0 引用数: 0
h-index: 0
机构: IRBM, MRL Rome, Dept Chem, I-00040 Rome, Italy

Brunetti, M
论文数: 0 引用数: 0
h-index: 0
机构: IRBM, MRL Rome, Dept Chem, I-00040 Rome, Italy

Altamura, S
论文数: 0 引用数: 0
h-index: 0
机构: IRBM, MRL Rome, Dept Chem, I-00040 Rome, Italy

De Francesco, R
论文数: 0 引用数: 0
h-index: 0
机构: IRBM, MRL Rome, Dept Chem, I-00040 Rome, Italy

Matassa, VG
论文数: 0 引用数: 0
h-index: 0
机构: IRBM, MRL Rome, Dept Chem, I-00040 Rome, Italy
[27]
Low-calcemic, highly antiproliferative, 1-difluoromethyl hybrid analogs of the natural hormone 1α,25-dihydroxyvitamin D3:: Design, synthesis, and preliminary biological evaluation
[J].
Peleg, Sara
;
Petersen, Kimberly S.
;
Suh, Byung Chul
;
Dolan, Patrick
;
Agoston, Elin S.
;
Kensler, Thomas W.
;
Posner, Gary H.
.
JOURNAL OF MEDICINAL CHEMISTRY,
2006, 49 (25)
:7513-7517

Peleg, Sara
论文数: 0 引用数: 0
h-index: 0
机构: Johns Hopkins Univ, Sch Arts & Sci, Dept Chem, Baltimore, MD 21218 USA

Petersen, Kimberly S.
论文数: 0 引用数: 0
h-index: 0
机构: Johns Hopkins Univ, Sch Arts & Sci, Dept Chem, Baltimore, MD 21218 USA

Suh, Byung Chul
论文数: 0 引用数: 0
h-index: 0
机构: Johns Hopkins Univ, Sch Arts & Sci, Dept Chem, Baltimore, MD 21218 USA

Dolan, Patrick
论文数: 0 引用数: 0
h-index: 0
机构: Johns Hopkins Univ, Sch Arts & Sci, Dept Chem, Baltimore, MD 21218 USA

Agoston, Elin S.
论文数: 0 引用数: 0
h-index: 0
机构: Johns Hopkins Univ, Sch Arts & Sci, Dept Chem, Baltimore, MD 21218 USA

Kensler, Thomas W.
论文数: 0 引用数: 0
h-index: 0
机构: Johns Hopkins Univ, Sch Arts & Sci, Dept Chem, Baltimore, MD 21218 USA

Posner, Gary H.
论文数: 0 引用数: 0
h-index: 0
机构:
Johns Hopkins Univ, Sch Arts & Sci, Dept Chem, Baltimore, MD 21218 USA Johns Hopkins Univ, Sch Arts & Sci, Dept Chem, Baltimore, MD 21218 USA
[28]
SYNTHESIS AND ANTIMALARIAL ACTIVITIES OF SEVERAL FLUORINATED ARTEMISININ DERIVATIVES
[J].
PU, YM
;
TOROK, DS
;
ZIFFER, H
;
PAN, XQ
;
MESHNICK, SR
.
JOURNAL OF MEDICINAL CHEMISTRY,
1995, 38 (20)
:4120-4124

PU, YM
论文数: 0 引用数: 0
h-index: 0
机构: NIDDK,CHEM PHYS LAB,BETHESDA,MD 20892

TOROK, DS
论文数: 0 引用数: 0
h-index: 0
机构: NIDDK,CHEM PHYS LAB,BETHESDA,MD 20892

ZIFFER, H
论文数: 0 引用数: 0
h-index: 0
机构: NIDDK,CHEM PHYS LAB,BETHESDA,MD 20892

PAN, XQ
论文数: 0 引用数: 0
h-index: 0
机构: NIDDK,CHEM PHYS LAB,BETHESDA,MD 20892

MESHNICK, SR
论文数: 0 引用数: 0
h-index: 0
机构: NIDDK,CHEM PHYS LAB,BETHESDA,MD 20892
[29]
Fluorous peptides get ready to heal
[J].
Ritter, Stephen K.
.
CHEMICAL & ENGINEERING NEWS,
2007, 85 (37)
:36-37

Ritter, Stephen K.
论文数: 0 引用数: 0
h-index: 0
[30]
Stabilization of bzip peptides through incorporation of fluorinated aliphatic residues
[J].
Son, Soojin
;
Caglar Tanrikulu, I.
;
Tirrell, David A.
.
CHEMBIOCHEM,
2006, 7 (08)
:1251-1257

Son, Soojin
论文数: 0 引用数: 0
h-index: 0
机构:
CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA

Caglar Tanrikulu, I.
论文数: 0 引用数: 0
h-index: 0
机构:
CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA

Tirrell, David A.
论文数: 0 引用数: 0
h-index: 0
机构:
CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA