PHOTOCHEMICAL MODIFICATION OF GLYCINE DIPEPTIDES

被引：29
作者：
ELAD, D
SPERLING, J
机构：
[1] Department of Chemistry, Weizmann Institute of Science, Rehovoth
来源：
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC | 1969年 / 11期
关键词：
D O I：
10.1039/j39690001579
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The acetone-initiated photochemical alkylation of protected glycylglycine, glycylalanine, and glycyl-leucine dipeptide methyl esters with isobutene, but-1-ene, and toluene is described. The reactions lead to the preferential conversion of the glycine residue to leucine, norleucine, or phenylalanine, respectively, in yields of up to 60%. A free-radical chain mechanism is proposed for these reactions.
引用
收藏
页码：1579 / &
相关论文
共 30 条
[1]   SYNTHETIC ASPECTS OF FREE-RADICAL ADDITION .2. PREPARATION OF HOMOLOGUES BY HOMOLYTIC ALKYLATION OF ACETIC ACID AND RELATED COMPOUNDS [J].
ALLEN, JC ;
CADOGAN, JIG ;
HEY, DH .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (MAR) :1918-&
[2]  
APFELDERFER BZ, 1968, THESIS WEIZMANN I SC
[3]   CHLORINE-ACTIVATION BY REDOX-TRANSFER .3. ABNORMAL ADDITION OF CHLOROFORM TO OLEFINS [J].
ASSCHER, M ;
VOFSI, D .
JOURNAL OF THE CHEMICAL SOCIETY, 1963, (AUG) :3921-&
[4]   CHLORINE ACTIVATION BY REDOX TRANSFER .2. ADDITION OF CARBON TETRACHLORIDE TO OLEFINS [J].
ASSCHER, M ;
VOFSI, D .
JOURNAL OF THE CHEMICAL SOCIETY, 1963, (MAR) :1887-&
[5]  
DETERMANN H, 1966, LIEBIGS ANN CHEM, V694, P190
[6]   PHOTO-INDUCED ALKYLATION OF GLYCINE RESIDUES IN DIPEPTIDES [J].
ELAD, D ;
SPERLING, J .
CHEMICAL COMMUNICATIONS, 1968, (11) :655-&
[7]   PHOTOALKYLATION OF GLYCINE DERIVATIVES [J].
ELAD, D ;
SINNREIC.J .
CHEMICAL COMMUNICATIONS, 1965, (19) :471-&
[8]   LIGHT-INDUCED AMIDATION OF TERMINAL OLEFINS [J].
ELAD, D ;
ROKACH, J .
JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (07) :1855-&
[9]   PHOTOALKYLATION OF GAMMA-BUTYROLACTONE WITH OLEFINS [J].
ELAD, D ;
FRIEDMAN, G ;
YOUSSEFY.RD .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (07) :870-&
[10]  
ELAD D, 1969, CHEM COMMUN, P234
123