Access to the inaccessible sequence of Cpn 60.1 (195-217) by temporary oxazolidine protection of selected amide bonds

被引：16

作者：

Keller, M ^{[1
]}

Miller, AD ^{[1
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, Imperial Coll Genet Therapies Ctr, S Kensington SW7 2AY, England

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2001年 / 11卷 / 06期

关键词：

D O I：

10.1016/S0960-894X(01)00085-3

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The solid-phase peptide synthesis of a reportedly inaccessible peptide sequence of chaperonin 60.1 (195-219) is described using oxazolidine containing dipeptide building blocks ('pseudo-proline' dipeptide units). Two attempts at the synthesis of the chaperonin 60.1 sequence are outlined using one and two pseudo-proline units, respectively, and these results are compared with the outcome of an ordinary stepwise (double) coupling procedure. The only successful synthesis is that combining two pseudo-proline building blocks. (C) 2001 Elsevier Science Ltd. AII rights reserved.

引用

收藏

页码：857 / 859

页数：3

相关论文

共 23 条

[1] Chaperonins in health and disease [J].

Coates, ARM ;

Henderson, B .

STRESS OF LIFE: FROM MOLECULES TO MAN, 1998, 851 :48-53

[2]

Cooper RG, 1999, ANGEW CHEM INT EDIT, V38, P1949, DOI 10.1002/(SICI)1521-3773(19990712)38:13/14<1949::AID-ANIE1949>3.0.CO

[3]

2-S

[4] Pseudo-prolines as a molecular hinge: Reversible induction of cis amide bonds into peptide backbones [J].

Dumy, P ;

Keller, M ;

Ryan, DE ;

Rohwedder, B ;

Wohr, T ;

Mutter, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (05) :918-925

[5] Enhancing the proline effect:: Pseudo-prolines for tailoring cis/trans isomerization [J].

Keller, M ;

Sager, C ;

Dumy, P ;

Schutkowski, M ;

Fischer, GS ;

Mutter, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (12) :2714-2720

[6] Orthogonal ligation of unprotected peptide segments through pseudoproline formation for the synthesis of HIV-1 protease [J].

Liu, CF ;

Rao, C ;

Tam, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (02) :307-312

[7] PEPTIDE SEGMENT LIGATION STRATEGY WITHOUT USE OF PROTECTING GROUPS [J].

LIU, CF ;

TAM, JP .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1994, 91 (14) :6584-6588

[8] Mycobacterium tuberculosis chaperonin 10 stimulates bone resorption: A potential contributory factor in Pott's disease [J].

Meghji, S ;

White, PA ;

Nair, SP ;

Reddi, K ;

Heron, K ;

Henderson, B ;

Zaliani, A ;

Fossati, G ;

Mascagni, P ;

Hunt, JF ;

Roberts, MM ;

Coates, ARM .

JOURNAL OF EXPERIMENTAL MEDICINE, 1997, 186 (08) :1241-1246

[9]

Merrifield R. B., 1976, SCIENCE, V232, P341, DOI DOI 10.1126/SCIENCE.3961484

[10] Bidirectional tandem pseudoproline ligations of proline-rich helical peptides [J].

Miao, ZW ;

Tam, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (18) :4253-4260