Oxidative phenol coupling - tyrosine dimers and libraries containing tyrosyl peptide dimers

被引：111

作者：

Eickhoff, H ^{[1
]}

Jung, G ^{[1
]}

Rieker, A ^{[1
]}

机构：

[1] Univ Tubingen, Inst Organ Chem, D-72076 Tubingen, Germany

来源：

TETRAHEDRON | 2001年 / 57卷 / 02期

关键词：

amino acids and derivatives; biaryls; oxidation; peptide analogues/mimetics;

D O I：

10.1016/S0040-4020(00)00942-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The principles of phenol oxidation are outlined and summarized. Various procedures were used to dimerize tyrosine derivatives, especially linear tripeptides and cyclohexapeptides, via cross-linking of their phenolic side-chains. The coupling was performed by potassium hexacyanoferrate(III), phenyliodine(III)-bis(trifluoroacetate), vanadium(V)-oxyfluoride or horseradish peroxidase. The individual dityrosine and isodityrosine derivatives obtained in preparative scale, as well as the peptide-dimer libraries generated, were characterized by HPLC and electrospray ionization mass spectrometry. Further analyses were carried out by NMR spectroscopy, fluorescence spectroscopy and gas chromatography. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：353 / 364

页数：12

共 122 条

[1] AMADO R, 1984, METHOD ENZYMOL, V107, P377
[2] ANWER MK, 1980, SYNTHESIS-STUTTGART, P929
[3] OXIDATIVE COUPLING OF PHENOLS .9. THE ROLE OF STERIC EFFECTS IN THE OXIDATION OF METHYL-SUBSTITUTED PHENOLS
ARMSTRONG, DR
CAMERON, C
NONHEBEL, DC
PERKINS, PG
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1983, (05): : 581 - 585
[4] THE CONSTRUCTION AND USE OF POTENTIAL-PH DIAGRAMS IN ORGANIC OXIDATION-REDUCTION REACTIONS
BAILEY, SI
RITCHIE, IM
HEWGILL, FR
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1983, (05): : 645 - 652
[5] Battersby AR, 1967, OXIDATIVE COUPLING P
[6] LEAD(IV) ESTER AND ELECTROCHEMICAL OXIDATIONS OF PHENOLIC-COMPOUNDS - A COMPARATIVE-STUDY
BEGLEY, MJ
GILL, BG
PATTENDEN, G
STAPLETON, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (07): : 1677 - 1683
[7] A NOVEL SYNTHESIS OF K-13
BEUGELMANS, R
BIGOT, A
ZHU, JP
[J]. TETRAHEDRON LETTERS, 1994, 35 (40) : 7391 - 7394
[8] Total synthesis of an antitumor agent RA-VII via an efficient preparation of cycloisodityrosine
Bigot, A
Elise, M
Dau, TH
Zhu, JP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (17) : 6283 - 6296
[9] Vancomycin CD and DE macrocyclization and atropisomerism studies
Boger, DL
Castle, SL
Miyazaki, S
Wu, JH
Beresis, RT
Loiseleur, O
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (01) : 70 - 80
[10] Alternative synthesis of the cycloisodityrosine subunit of deoxybouvardin, RA-VII, and related agents: Reassignment of the stereochemistry of prior intermediates
Boger, DL
Zhou, JC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (12) : 3938 - 3939

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