SYNTHESIS AND CHARACTERIZATION OF SOME NEW N-NITROSODIPEPTIDES

被引:9
作者
CHALLIS, BC
MILLIGAN, JR
MITCHELL, RC
机构
[1] UNIV LONDON IMPERIAL COLL SCI & TECHNOL,DEPT CHEM,LONDON SW7 2AZ,ENGLAND
[2] SK&F LABS LTD,WELWYN GARDEN CIT L7 1EY,HERTS,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 11期
关键词
D O I
10.1039/p19900003103
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of 11 new N-nitrosodipeptides by aprotic nitrosation with N2O4 is described for N(N'-acetyl-L-prolyl)glycine, -L-alanine, -L-phenylalanine; and N-phthalimidoacetylglycine peptides and their (benzyl or ethyl) esters. The UV-vis, IR, 1H NMR and MS properties of the new Nnitrosodipeptides are reported and their structural significance is analysed.
引用
收藏
页码:3103 / 3108
页数:6
相关论文
共 21 条
[1]   MUTAGENIC PROPERTIES OF N-NITROSOPEPTIDES IN MAMMALIAN-CELL CULTURE ASSAYS [J].
ANDERSON, D ;
PHILLIPS, BJ ;
CHALLIS, BC ;
HOPKINS, AR ;
MILLIGAN, JR ;
MASSEY, RC .
FOOD AND CHEMICAL TOXICOLOGY, 1986, 24 (04) :289-292
[2]   ENVIRONMENTAL FACTORS AND CANCER INCIDENCE AND MORTALITY IN DIFFERENT COUNTRIES, WITH SPECIAL REFERENCE TO DIETARY PRACTICES [J].
ARMSTRONG, B ;
DOLL, R .
INTERNATIONAL JOURNAL OF CANCER, 1975, 15 (04) :617-631
[3]   EFFECTS OF THE NITROSOPEPTIDE N-(N-ACETYL-L-PROLYL)-N-NITROSOGLYCINE ON SALMONELLA-TYPHIMURIUM TA100 IN THE HOST-MEDIATED ASSAY IN MICE [J].
BLOWERS, SD ;
BRINKWORTH, MH ;
ANDERSON, D .
FOOD AND CHEMICAL TOXICOLOGY, 1988, 26 (11-12) :917-919
[4]   THE INVIVO GENOTOXIC PROPERTIES OF THE NITROSOPEPTIDE N-(N-ACETYL-L-PROLYL)-N-NITROSOGLYCINE [J].
BLOWERS, SD ;
ANDERSON, D .
FOOD AND CHEMICAL TOXICOLOGY, 1988, 26 (09) :785-790
[5]   NITROSATION AND NITROSYLATION OF HEMOPROTEINS AND RELATED COMPOUNDS .2. REACTION OF NITROUS-ACID WITH THE SIDE-CHAINS OF ALPHA-ACYL-AMINO-ACID ESTERS [J].
BONNETT, R ;
NICOLAIDOU, P .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (08) :1969-1974
[6]   REACTION OF ACIDIFIED NITRITE SOLUTIONS WITH PEPTIDE DERIVATIVES - EVIDENCE FOR NITROSAMINE AND THIONITRITE FORMATION FROM N-15 NMR-STUDIES [J].
BONNETT, R ;
HOLLEYHEAD, R ;
JOHNSON, BL ;
RANDALL, EW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (22) :2261-2264
[7]   THE MUTAGENIC PROPERTIES OF N-NITROSOPEPTIDES IN THE AMES TEST [J].
CHALLIS, BC ;
HOPKINS, AR ;
MILLIGAN, JR ;
MASSEY, RC ;
ANDERSON, D ;
BLOWERS, SD .
TOXICOLOGY LETTERS, 1985, 26 (2-3) :89-93
[8]   SYNTHESIS AND STABILITY OF N-NITROSODIPEPTIDES [J].
CHALLIS, BC ;
MILLIGAN, JR ;
MITCHELL, RC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (16) :1050-1051
[9]   REARRANGEMENT OF CARBOXYLATES DERIVED FROM N-ACETYL-N-NITROSO-ALPHA-AMINO-ACIDS [J].
CHOW, YL ;
POLO, J .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (06) :297-299
[10]  
CHOW YL, 1984, IARC SCI PUBLN, V57, P317