Chemoenzymatic Synthesis of (S)-Hexafluoroleucine and (S)-Tetrafluoroleucine

被引:21
作者
Chiu, Hsien-Po [1 ]
Cheng, Richard P. [1 ]
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.
引用
收藏
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
[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
[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
[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
[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
[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
[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
[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
[29]   Fluorous peptides get ready to heal [J].
Ritter, Stephen K. .
CHEMICAL & ENGINEERING NEWS, 2007, 85 (37) :36-37
[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