SYNTHESIS OF LEU-ABU(P) AND GLU-ABU(P)-LEU - ISOSTERES OF SER(P)-PEPTIDES

被引:28
作者
TONG, G [1 ]
PERICH, JW [1 ]
JOHNS, RB [1 ]
机构
[1] UNIV MELBOURNE,DEPT ORGAN CHEM,PARKVILLE,VIC 3052,AUSTRALIA
关键词
D O I
10.1016/S0040-4039(00)97464-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Boc-Asp-Ot-Bu was efficiently converted to Boc-Abu(PO3Me2)-Ot-Bu in five steps then to Boc-Abu(PO3Me2)-OH in two steps. Both the protected amino acids were used in the syntheses of Boc-Leu-Abu(PO3Me2)-Ot-Bu and Boc-Glu(OBzl)-Abu(PO3Me2)-Leu-OBzl by the Boc mode of peptide synthesis. These were deprotected to Leu-Abu(P) and Glu-Abu(P)-Leu by hydrogenolysis followed by bromotimethylsilane treatment. © 1990.
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收藏
页码:3759 / 3762
页数:4
相关论文
共 11 条
[1]   A NOVEL-APPROACH TO PHOSPHOPEPTIDE SYNTHESIS-PREPARATION OF GLU-PSER-LEU [J].
ALEWOOD, PF ;
PERICH, JW ;
JOHNS, RB .
TETRAHEDRON LETTERS, 1984, 25 (09) :987-990
[2]  
ANELLI PL, 1987, J ORG CHEM, V52, P2559
[3]   PHOSPHONATES AS ANALOGS OF NATURAL PHOSPHATES [J].
ENGEL, R .
CHEMICAL REVIEWS, 1977, 77 (03) :349-367
[4]   NEW SILICON-PHOSPHORUS REAGENTS IN ORGANIC-SYNTHESIS - CARBONYL AND CONJUGATE ADDITION-REACTIONS OF SILICON PHOSPHITE ESTERS AND RELATED SYSTEMS [J].
EVANS, DA ;
HURST, KM ;
TAKACS, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (11) :3467-3477
[5]  
MCKENNA CE, 1977, TETRAHEDRON LETT, P155
[6]   SOLUTION PHASE SYNTHESIS OF AN O-PHOSPHOSERYL-CONTAINING PEPTIDE USING PHENYL PHOSPHOROTRIESTER PROTECTION [J].
PERICH, JW ;
ALEWOOD, PF ;
JOHNS, RB .
TETRAHEDRON LETTERS, 1986, 27 (12) :1373-1376
[7]  
PERICH JW, 1990, PEPTIDES PROTEIN PHO, pCH10
[9]  
SOAI K, 1987, SYNTHESIS-STUTTGART, P647
[10]  
VALERIO RM, 1988, SYNTHESIS-STUTTGART, P786