TRYPTOPHAN-CONTAINING 1,5-TETRAZOLE DIPEPTIDE ANALOGS - SYNTHESIS OF TRP-PSI[CN4]NLE AS A CIS AMIDE BOND SURROGATE

被引：20

作者：

BOTEJU, LW ^{[1
]}

HRUBY, VJ ^{[1
]}

机构：

[1] UNIV ARIZONA,DEPT CHEM,TUCSON,AZ 85721

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 11期

关键词：

D O I：

10.1016/S0040-4039(00)60771-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 1,5-disubstituted tetrazole dipeptide analog Z-Trp(N(in)Z)PSI[CN4]Nle-OBzl was synthesized in good yield and high optical purity using a modified procedure of Zabrocki et al. This dipeptide analog can be selectively deprotected at either the N or the C terminal for further incorporation into peptides.

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页码：1757 / 1760

页数：4

相关论文

共 10 条

[1]

FANG SN, 1991, PEPTIDES STRUCTURE B, P63

[2]

HRUBY VJ, 1990, INT J PEPT PROT RES, V35, P566

[3] CROWN ETHERS AS CATALYSTS OF FLUORIDE-ANION-MEDIATED REACTIONS IN PEPTIDE-SYNTHESIS .1. PROTECTION OF TRYPTOPHAN BY BENZYLOXYCARBONYL AND 2,4-DICHLOROBENZYLOXYCARBONYL GROUPS [J].

KLAUSNER, YS ;

CHOREV, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (06) :627-631

[4] S-CIS AND S-TRANS ISOMERISM OF THE HIS-PRO PEPTIDE-BOND IN ANGIOTENSIN AND THYROLIBERIN ANALOGS [J].

LIAKOPOULOUKYRIAKIDES, M ;

GALARDY, RE .

BIOCHEMISTRY, 1979, 18 (10) :1952-1957

[5]

Marshall G. R., 1981, PEPTIDES SYNTHESIS S, P669

[6] ONE-POT CONVERSION OF N-BENZYLOXYCARBONYL GROUP INTO N-TERT-BUTOXYCARBONYL GROUP [J].

SAKAITANI, M ;

HORI, K ;

OHFUNE, Y .

TETRAHEDRON LETTERS, 1988, 29 (24) :2983-2984

[7] C-13 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY AND CIS-TRANS ISOMERISM IN DIPEPTIDES CONTAINING PROLINE [J].

THOMAS, WA ;

WILLIAMS, MK .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (17) :994-&

[8] SYNTHESIS AND CHEMICAL-PROPERTIES OF TETRAZOLE PEPTIDE ANALOGS [J].

YU, KL ;

JOHNSON, RL .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (10) :2051-2059

[9] CONFORMATIONAL MIMICRY .1. 1,5-DISUBSTITUTED TETRAZOLE RING AS A SURROGATE FOR THE CIS AMIDE BOND [J].

ZABROCKI, J ;

SMITH, GD ;

DUNBAR, JB ;

IIJIMA, H ;

MARSHALL, GR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (17) :5875-5880

[10] CONFORMATIONAL MIMICRY .3. SYNTHESIS AND INCORPORATION OF 1,5-DISUBSTITUTED TETRAZOLE DIPEPTIDE ANALOGS INTO PEPTIDES WITH PRESERVATION OF CHIRAL INTEGRITY - BRADYKININ [J].

ZABROCKI, J ;

DUNBAR, JB ;

MARSHALL, KW ;

TOTH, MV ;

MARSHALL, GR .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (01) :202-209