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
[11]   MEASUREMENT OF RACEMIZATION IN PEPTIDE SYNTHESIS BY NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY [J].
HALPERN, B ;
CHEW, LF ;
WEINSTEIN, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (19) :5051-+
[12]   PHOTOCHEMISTRY OF BIOLOGICAL MOLECULES .2. PHOTOLYSIS OF DIPEPTIDES IN SOLID STATE [J].
JOHNS, RB ;
LOONEY, FD ;
WHELAN, DJ .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1968, 7 (01) :65-&
[13]   PHOTOCHEMISTRY OF BIOLOGICAL MOLECULES .I. PHOTOLYSIS OF AMINO ACIDS IN SOLID STATE [J].
JOHNS, RB ;
LOONEY, FD ;
WHELAN, DJ .
BIOCHIMICA ET BIOPHYSICA ACTA, 1967, 147 (02) :369-&
[14]   MECHANISM OF ENZYME INACTIVATION BY ULTRAVIOLET LIGHT AND THE PHOTOCHEMISTRY OF AMINO ACIDS (AT 2537-A) [J].
LUSE, RA ;
MCLAREN, AD .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1963, 2 (03) :343-360
[15]  
MCLAREN AD, 1964, PHOTOCHEMISTRY PROTE, P29
[16]   STUDY OF RADICALS DERIVED FROM GLYCINE AND ALANINE IN SOLUTION [J].
POUPKO, R ;
SILVER, BL ;
LOWENSTE.A .
CHEMICAL COMMUNICATIONS, 1968, (08) :453-&
[17]  
PRYOR WA, 1966, FREE RADICALS, P17
[18]  
PRYOR WA, 1966, FREE RADICALS, P13
[19]  
PULLMAN A, 1965, MODERN QUANTUM CHEM, V3, P283
[20]  
RAM JS, 1962, ADV ENZYMOL REL S BI, V24, P105