Development of a hypusine reagent for peptide synthesis

被引：18

作者：

Bergeron, RJ

Ludin, C

Muller, R

Smith, RE

Phanstiel, O

机构：

[1] UNIV BERN,INST ORGAN CHEM,CH-3012 BERN,SWITZERLAND

[2] UNIV CENT FLORIDA,DEPT CHEM,ORLANDO,FL 32816

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 10期

关键词：

D O I：

10.1021/jo970119z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a reagent that enables the incorporation of the unusual amino acid (2S,9R)hypusine (Hpu) into peptide sequences is described. The reagent, (2S,SR)-11-[(benzyloxycarbonyl)amino]-7-(carbobenzyloxy)-2- [(9-fluorenylmethoxycarbonyl)amino]-9-(tetrahydropyran-2-yloxy)- 7-azaundecanoic acid, is utilized in the synthesis of a hexapeptide containing the primary pentapeptide sequence of the eukaryotic initiation factor eIF-5A, L-Cys-L-Thr-Gly-Hpu-L-His-Gly. The reagent is shown to be effective for both solution phase and Merrifield resin synthesis.

引用

页码：3285 / 3290

页数：6

共 29 条

[1] INTERNATIONAL-SYMPOSIUM ON PROTEIN-SYNTHESIS - SUMMARY OF FOGARTY CENTER-NIH WORKSHOP HELD IN BETHESDA, MARYLAND ON 18-20 OCTOBER, 1976
ANDERSON, WF
BOSCH, L
COHN, WE
LODISH, H
MERRICK, WC
WEISSBACH, H
WITTMANN, HG
WOOL, IG
[J]. FEBS LETTERS, 1977, 76 (01) : 1 - 10
[2] Barlos K, 1996, INT J PEPT PROT RES, V47, P148
[3] FMOC-HIS(MMT)-OH AND FMOC-HIS(MTT)-OH - 2 NEW HISTIDINE DERIVATIVES N(IM) PROTECTED WITH HIGHLY ACID-SENSITIVE GROUPS - PREPARATION, PROPERTIES AND USE IN PEPTIDE-SYNTHESIS
BARLOS, K
CHATZI, O
GATOS, D
STAVROPOULOS, G
TSEGENIDIS, T
[J]. TETRAHEDRON LETTERS, 1991, 32 (04) : 475 - 478
[4] TOTAL SYNTHESES OF (+)-HYPUSINE AND ITS (2S,9S)-DIASTEREOMER
BERGERON, RJ
XIA, MXB
PHANSTIEL, O
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (24) : 6804 - 6806
[5] A general procedure of the peptide synthesis.
Bergmann, M
Zervas, L
[J]. BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1932, 65 (07): : 1192 - 1201
[6] PROSTAGLANDINS AND CONGENERS .20. SYNTHESIS OF PROSTAGLANDINS VIA CONJUGATE ADDITION OF LITHIUM TRANS-1-ALKENYLTRIALKYLALANATE REAGENTS - NOVEL REAGENT FOR CONJUGATE 1,4-ADDITIONS
BERNADY, KF
FLOYD, MB
POLETTO, JF
WEISS, MJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (09) : 1438 - 1447
[7] Inhibition of HIV-1 replication in lymphocytes by mutants of the Rev cofactor eIF-5A
Bevec, D
Jaksche, H
Oft, M
Wohl, T
Himmelspach, M
Pacher, A
Schebesta, M
Koettnitz, K
Dobrovnik, M
Csonga, R
Lottspeich, F
Hauber, J
[J]. SCIENCE, 1996, 271 (5257) : 1858 - 1860
[8] RAPID CONTINUOUS PEPTIDE-SYNTHESIS VIA FMOC AMINO-ACID CHLORIDE COUPLING AND 4-(AMINOMETHYL)PIPERIDINE DEBLOCKING
BEYERMANN, M
BIENERT, M
NIEDRICH, H
CARPINO, LA
SADATAALAEE, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (02) : 721 - 728
[9] CYANOHYDRIDOBORATE ANION AS A SELECTIVE REDUCING AGENT
BORCH, RF
BERNSTEIN, MD
DURST, HD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (12) : 2897 - +
[10] IDENTIFICATION OF THE HYPUSINE-CONTAINING PROTEIN HY+ AS TRANSLATION INITIATION-FACTOR EIF-4D
COOPER, HL
PARK, MH
FOLK, JE
SAFER, B
BRAVERMAN, R
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES, 1983, 80 (07): : 1854 - 1857

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