Synthesis of novel acetylene-containing amino acids

被引：19

作者：

IJsselstijn, M

Kaiser, J

van Delft, FL

Schoemaker, HE

Rutjes, FPJT

机构：

[1] Univ Nijmegen, Dept Organ Chem, NL-6525 ED Nijmegen, Netherlands

[2] DSM Res & Patents, Life Sci Prod, Geleen, Netherlands

来源：

AMINO ACIDS | 2003年 / 24卷 / 03期

关键词：

organozinc reagent; alkyne metathesis; non-proteinogenic amino acids; unsaturated amino acids; acetylenic amino acids; beta-turn mimic;

D O I：

10.1007/s00726-002-0408-3

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Novel synthetic procedures for the modification of non-proteinogenic acetylene-containing amino acids have been developed. The functionalization either proceeds via zinc/copper-mediated introduction of alkyl substituents, or via tungsten-catalyzed ring-closing alkyne metathesis reactions.

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页码：263 / 266

页数：4

相关论文

共 17 条

[1] Synthesis of diaminosuberic acid derivatives via ring-closing alkyne metathesis [J].

Aguilera, B ;

Wolf, LB ;

Nieczypor, P ;

Rutjes, FPJT ;

Overkleeft, HS ;

van Hest, JCM ;

Schoemaker, HE ;

Wang, B ;

Mol, JC ;

Fürstner, A ;

Overhand, M ;

van der Marel, GA ;

van Boom, JH .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (10) :3584-3589

[2]

ALTER R, 1974, P NATL ACAD SCI USA, V74, P1901

[3]

[Anonymous], 2000, J CHEM SOC PERKIN T

[4] Design, synthesis, and conformational analysis of a proposed type I β-turn mimic [J].

Fink, BE ;

Kym, PR ;

Katzenellenbogen, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (18) :4334-4344

[5]

Fürstner A, 2001, CHEM-EUR J, V7, P5299, DOI 10.1002/1521-3765(20011217)7:24<5299::AID-CHEM5299>3.0.CO

[6]

2-X

[7]

Hofmeister H., 1984, ANGEW CHEM, V96, P720

[8] Concise synthesis of enantiomerically pure phenylalanine, homophenylalanine, and bishomophenylalanine derivatives using organozinc chemistry: NMR studies of amino acid-derived organozinc reagents [J].

Jackson, RFW ;

Moore, RJ ;

Dexter, CS ;

Elliot, J ;

Mowbray, CE .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :7875-7884

[9]

JUNG G, 1996, COMBINATORIAL PEPTID

[10] Thrombin inhibitors based on a propargylglycine template [J].

Lee, K ;

Hwang, SY ;

Park, CW .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (07) :1013-1018