A new ligand α-amino acid:: (S)-2-amino-3-[1-(1,4,7-triazacyclononane)]propanoic acid

被引：27

作者：

Rossi, P

Felluga, F

Scrimin, P

机构：

[1] Univ Padua, Dept Organ Chem, I-35131 Padua, Italy

[2] CNR, CMRO, I-35131 Padua, Italy

[3] Univ Trieste, Dept Chem Sci, I-34127 Trieste, Italy

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 39期

关键词：

D O I：

10.1016/S0040-4039(98)01532-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title amino acid was obtained by regiospecific ring-opening reaction of Boc-diprotected 1,4,7-triazacyclononane with (S)-2-beazyloxycarbonylamino-beta-lactone 80% isolated yield) followed by deprotection. It strongly binds transition metal ions like Zn and Cu-II and can be incorporated in peptide sequences without affecting the metal ion affinity of the triazamacrocycle. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：7159 / 7162

页数：4

相关论文

共 20 条

[1] CONVERSION OF SERINE TO STEREOCHEMICALLY PURE BETA-SUBSTITUTED ALPHA-AMINO-ACIDS VIA BETA-LACTONES [J].

ARNOLD, LD ;

KALANTAR, TH ;

VEDERAS, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (24) :7105-7109

[2]

Brandes S, 1996, B SOC CHIM FR, V133, P65

[3] Peptide synthesis via amino acid halides [J].

Carpino, LA ;

Beyermann, M ;

Wenschuh, H ;

Bienert, M .

ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (06) :268-274

[4] Metallopeptide design: Tuning the metal cation affinities with unnatural amino acids and peptide secondary structure [J].

Cheng, RP ;

Fisher, SL ;

Imperiali, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (46) :11349-11356

[5] Mechanistic studies of dichloro(1,4,7-triazacyclononane)copper(II)-catalyzed phosphate diester hydrolysis [J].

Deal, KA ;

Burstyn, JN .

INORGANIC CHEMISTRY, 1996, 35 (10) :2792-2798

[6] METAL-ION DEPENDENT MODULATION OF THE DYNAMICS OF A DESIGNED PROTEIN [J].

HANDEL, TM ;

WILLIAMS, SA ;

DEGRADO, WF .

SCIENCE, 1993, 261 (5123) :879-885

[7] HYDROLYSIS OF UNACTIVATED PEPTIDE-BONDS BY A MACROCYCLIC COPPER(II) COMPLEX - CU([9]ANEN(3))CL-2 HYDROLYZES BOTH DIPEPTIDES AND PROTEINS [J].

HEGG, EL ;

BURSTYN, JN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (26) :7015-7016

[8] CHEMOENZYMATIC SYNTHESIS OF 2-AMINO-3-(2,2'-BIPYRIDINYL)PROPANOIC ACIDS [J].

IMPERIALI, B ;

PRINS, TJ ;

FISHER, SL .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (06) :1613-1616

[9] (S)-ALPHA-AMINO-2,2'-BIPYRIDINE-6-PROPANOIC ACID - A VERSATILE AMINO-ACID FOR DENOVO METALLOPROTEIN DESIGN [J].

IMPERIALI, B ;

FISHER, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) :8527-8528

[10] NOVEL METAL-BINDING PROTEINS BY DESIGN [J].

KLEMBA, M ;

GARDNER, KH ;

MARINO, S ;

CLARKE, ND ;

REGAN, L .

NATURE STRUCTURAL BIOLOGY, 1995, 2 (05) :368-373