Dipeptides bearing nucleobases for the synthesis of novel peptide nucleic acids

被引：24

作者：

Lowe, G

Vilaivan, T

机构：

[1] Dyson Perrins Laboratory, Oxford University, Oxford OX1 3QY, South Parks Road

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 04期

关键词：

D O I：

10.1039/a603699f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Three stereoisomers (cis-L, trans-D and cis-D) of N-Fmoc-glycyl-4-(thymin-1-yl)proline and their pentafluorophenyl esters have been prepared for use in the synthesis of novel peptide nucleic acids. In addition, N-Fmoc-glycyl-4(N-6-benzoyladenin-9-yl)proline, N-Fmoc-glycyl-4-(N-4-benzoylcytosin-1-yl)proline and N-Fmoc-glycyl-4-(N-2-isobutyrylguanin-9-yl)proline and their pentafluorophenyl esters of the cis-D series have been synthesized.

引用

收藏

页码：547 / 554

页数：8

相关论文

共 21 条

[1] CLEAVAGE OF NORMAL-CARBOBENZOXY GROUPS BY DRY HYDROGEN BROMIDE AND HYDROGEN CHLORIDE [J].

BENISHAI, D ;

BERGER, A .

JOURNAL OF ORGANIC CHEMISTRY, 1952, 17 (12) :1564-1570

[2] THE STRUCTURES OF SOME ACYLCYTOSINES [J].

BROWN, DM ;

TODD, A ;

VARADARAJAN, S .

JOURNAL OF THE CHEMICAL SOCIETY, 1956, (JUL) :2384-2387

[3] CHEMISTRY OF CEPHALOSPORIN ANTIBIOTICS .21. CONVERSION OF PENICILLINS TO CEPHALEXIN [J].

CHAUVETT.RR ;

PENNINGT.PA ;

RYAN, CW ;

COOPER, RDG ;

JOSE, FL ;

WRIGHT, IG ;

VANHEYNI.EM ;

HUFFMAN, GW .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (09) :1259-&

[4] C-13 MAGNETIC-RESONANCE .25. BASIC SET OF PARAMETERS FOR INVESTIGATION OF TAUTOMERISM IN PURINES ESTABLISHED FROM C-13 MAGNETIC-RESONANCE STUDIES USING CERTAIN PURINES AND PYRROLO[2,3-D]PYRIMIDINES [J].

CHENON, MT ;

PUGMIRE, RJ ;

GRANT, DM ;

PANZICA, RP ;

TOWNSEND, LB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (16) :4627-4636

[5]

CLARK S, 1994, THESIS OXFORD U

[6] SOLID-PHASE PEPTIDE-SYNTHESIS UTILIZING 9-FLUORENYLMETHOXYCARBONYL AMINO-ACIDS [J].

FIELDS, GB ;

NOBLE, RL .

INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1990, 35 (03) :161-214

[7]

GREENE TW, 1991, PROTECTIVE GROUPS OR, P328

[8] SULFUR-CONTAINING POLYPEPTIDES .I. USE OF N-BENZHYDRYLOXYCARBONYL GROUP AND BENZHYDRYL ESTER [J].

HISKEY, RG ;

ADAMS, JB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (17) :3969-+

[9] CARBOCYCLIC ANALOGS OF NUCLEOSIDES .2. SYNTHESIS OF 2',3'-DIDEOXY-5'-HOMONUCLEOSIDE ANALOGS [J].

JENNY, TF ;

HORLACHER, J ;

PREVISANI, N ;

BENNER, SA .

HELVETICA CHIMICA ACTA, 1992, 75 (06) :1944-1954

[10] CARBOCYCLIC ANALOGS OF NUCLEOSIDES VIA MODIFIED MITSUNOBU REACTIONS [J].

JENNY, TF ;

PREVISANI, N ;

BENNER, SA .

TETRAHEDRON LETTERS, 1991, 32 (48) :7029-7032