Synthesis of a complete set of L-difluorophenylalanines, L-(F2)Phe, as molecular explorers for the CH/-π interaction between peptide ligand and receptor

被引：17

作者：

Fujita, T ^{[1
]}

Nose, T ^{[1
]}

Matsushima, A ^{[1
]}

Okada, K ^{[1
]}

Asai, D ^{[1
]}

Yamauchi, Y ^{[1
]}

Shirasu, N ^{[1
]}

Honda, T ^{[1
]}

Shigehiro, D ^{[1
]}

Shimohigashi, Y ^{[1
]}

机构：

[1] Kyushu Univ, Grad Sch Sci, Dept Mol Chem, Lab Struct Funct Biochem, Fukuoka 8128581, Japan

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 06期

关键词：

amino acids; amino acid derivatives; fluorine; fluorine compounds; molecular recognition; peptides; polypeptides;

D O I：

10.1016/S0040-4039(99)02191-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A complete set of difluorophenylalanines in the L-configuration [L-(F-2)Phe] (namely, L-(2,3-F-2)Phe, L-(2,4F(2))Phe, L-(2,5-F-2)Phe, L-(2,6-F-2)Phe, L-(3,4-F-2)Phe, L-(3,5-F-2)Phe) was prepared and incorporated into the thrombin receptor-tethered ligand peptide SFLLRNP to identify the phenyl hydrogens of the Phe-2 residue involved in the CH/pi receptor interaction. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：923 / 927

页数：5

共 9 条

[1] Hruby VJ, 1997, BIOPOLYMERS, V43, P219, DOI 10.1002/(SICI)1097-0282(1997)43:3<219::AID-BIP3>3.0.CO
[2] 2-Y
[3] TETRAHEDRON REPORT NUMBER-378 - THE CH/PI INTERACTION - SIGNIFICANCE IN MOLECULAR RECOGNITION
NISHIO, M
UMEZAWA, Y
HIROTA, M
TAKEUCHI, Y
[J]. TETRAHEDRON, 1995, 51 (32) : 8665 - 8701
[4] Interaction mode of the phe-phenyl group of thrombin receptor-tethered ligand SFLLRNP in receptor activation
Nose, T
Fujita, T
Nakajima, M
Inoue, Y
Costa, T
Shimohigashi, Y
[J]. JOURNAL OF BIOCHEMISTRY, 1998, 124 (02) : 354 - 358
[5] ENHANCEMENT OF THROMBIN RECEPTOR ACTIVATION BY THROMBIN RECEPTOR-DERIVED HEPTAPEPTIDE WITH PARA-FLUOROPHENYLALANINE IN PLACE OF PHENYLALANINE
NOSE, T
SHIMOHIGASHI, Y
OHNO, M
COSTA, T
SHIMIZU, N
OGINO, Y
[J]. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1993, 193 (02) : 694 - 699
[6] PRUDCHEKO AT, 1970, IZV SIB OTD AN KHIM, P95
[7] RESOLUTION OF AMINO-ACIDS .12. PREPARATION OF L-2-AMINO-5-ARYLPENTANOIC ACIDS, CONSTITUENT AMINO-ACIDS IN AM-TOXINS
SHIMOHIGASHI, Y
LEE, S
IZUMIYA, N
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1976, 49 (11) : 3280 - 3284
[8] Shimohigashi Y, 1986, NIDA Res Monogr, V69, P65
[9] Tolman V., 1995, FLUORINE CONTAINING, P1

← 1 →