A facile and efficient synthesis of (purin-6-yl)alanines

被引:28
作者
Capek, P [1 ]
Pohl, R [1 ]
Hocek, M [1 ]
机构
[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, CZ-16610 Prague 6, Czech Republic
关键词
D O I
10.1021/jo048812r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(Purin-6-yl)alanines, a new class of amino acid-nucleobase conjugates, were synthesized by palladium-catalyzed cross-coupling reactions of protected iodozincalanines with 6-iodopurines (9-Bn-6-iodopurine and 9-THP-6-iodopurine as well as acyl-protected 6-iodopurine ribonucleoside and 2-deoxyribonucleoside). Free purine base and nucleosides bearing alanine in position 6 were obtained after complete deprotection of the products of cross-coupling reactions.
引用
收藏
页码:7985 / 7988
页数:4
相关论文
共 33 条
[1]   Palladium-assisted routes to nucleosides [J].
Agrofoglio, LA ;
Gillaizeau, I ;
Saito, Y .
CHEMICAL REVIEWS, 2003, 103 (05) :1875-1916
[2]   Cytotoxic and antibacterial activity of 2-oxopurine derivatives [J].
Andresen, G ;
Gundersen, LL ;
Nissen-Meyer, J ;
Rise, F ;
Spilsberg, B .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (04) :567-569
[3]   9-benzylpurines with inhibitory activity against Mycobacterium tuberculosis [J].
Bakkestuen, AK ;
Gundersen, LL ;
Langli, G ;
Liu, FS ;
Nolsoe, JMJ .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (11) :1207-1210
[4]  
CHAMAN ES, 1963, ZH OBSHCH KHIM+, V33, P3342
[5]  
CHAMAN ES, 1966, ZH OBSHCH KHIM, V36, P1608
[6]   Direct synthesis of Fmoc-protected amino acids using organozinc chemistry: application to polymethoxylated phenylalanines and 4-oxoamino acids [J].
Deboves, HJC ;
Montalbetti, CAGN ;
Jackson, RFW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (16) :1876-1884
[7]  
DOW RL, 1994, SYNLETT, P293
[8]  
FRASER JL, 1994, SYNLETT, P379
[9]   Synthesis and antimycobacterial activity of 6-arylpurines:: The requirements for the N-9 substituent in active antimycobacterial purines [J].
Gundersen, LL ;
Nissen-Meyer, J ;
Spilsberg, B .
JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (06) :1383-1386
[10]   An unnatural base pair for incorporating amino acid analogs into proteins [J].
Hirao, I ;
Ohtsuki, T ;
Fujiwara, T ;
Mitsui, T ;
Yokogawa, T ;
Okuni, T ;
Nakayama, H ;
Takio, K ;
Yabuki, T ;
Kigawa, T ;
Kodama, K ;
Yokogawa, T ;
Nishikawa, K ;
Yokoyama, S .
NATURE BIOTECHNOLOGY, 2002, 20 (02) :177-182