Synthesis of monoprotected derivatives of homo-bifunctional molecules

被引:9
作者
Ehteshami, GR
Sharma, SD
Porath, J
Guzman, RZ [1 ]
机构
[1] Univ Arizona, Dept Environm Chem & Engn, Tucson, AZ 85721 USA
[2] Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
[3] Univ Arizona, Dept Biochem, Tucson, AZ 85721 USA
关键词
PEG; monoprotection; homo-bifunctional; hetero-bifunctional;
D O I
10.1016/S1381-5148(97)00078-3
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Selective derivatization of one of the two functional groups in a symmetrical homo-bifunctional molecule is always an uphill synthetic task. A novel method for synthesis of mono-protected homo-bifunctional poly(ethylene glycol) (PEG) is described in this work. The methodology utilizes a combination of two protecting groups that are orthogonal to each other for the introduction of one of these groups into symmetrical homo-bifunctional PEG polymers. Different well-known protecting groups, namely the carbobenzyloxy (Z) and the t-butyloxycarbonyl (Boc) groups, have been evaluated for this particular purpose. The approach appears to be straightforward in terms of separation of desired products from other non-desirable products or reactants. The methodology described here might be applicable to any symmetrical homo-bifunctional molecular substance and for synthesis of its corresponding monoprotected derivatives.
引用
收藏
页码:135 / 143
页数:9
相关论文
共 12 条
[1]  
BECKER H, 1982, MAKROMOL CHEM-RAPID, V3, P217
[2]  
FORD WT, 1986, ACS SYM SER, V308, P247
[3]  
FRECHET JMJ, 1980, POLYM SUPPORTED REAC, P293
[4]   DETERMINATION OF FREE AMINO GROUPS IN PROTEINS BY TRINITROBENZENESULFONIC ACID [J].
HABEEB, AFS .
ANALYTICAL BIOCHEMISTRY, 1966, 14 (03) :328-&
[5]  
Harris J.M., 1992, Polyethylene Glycol: Chemistry and Biological Applications
[6]   SYNTHESIS OF A STABLE COMPLEX OF A MACROCYCLE AND A THREADED CHAIN [J].
HARRISON, IT ;
HARRISON, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (22) :5723-&
[7]   USE OF INSOLUBLE POLYMER SUPPORTS IN GENERAL ORGANIC-SYNTHESIS [J].
LEZNOFF, CC .
ACCOUNTS OF CHEMICAL RESEARCH, 1978, 11 (09) :327-333
[8]   USE OF POLYMER SUPPORTS IN ORGANIC SYNTHESIS - SYNTHESIS OF MONOTRITYL ETHERS OF SYMMETRICAL DIOLS [J].
LEZNOFF, CC ;
WONG, JY .
CANADIAN JOURNAL OF CHEMISTRY, 1972, 50 (17) :2892-&
[9]   New derivatives of p-arsanilic acid part VII p-arsonoazelanilic and p-arsonosebacanilic acids and related compounds [J].
Morgan, GT ;
Walton, E .
JOURNAL OF THE CHEMICAL SOCIETY, 1936, :902-905
[10]   SYNTHESIS OF AN END-GROUP FUNCTIONALIZED POLYETHYLENE GLYCOL-LIPID CONJUGATE FOR PREPARATION OF POLYMER-GRAFTED LIPOSOMES [J].
ZALIPSKY, S .
BIOCONJUGATE CHEMISTRY, 1993, 4 (04) :296-299