APPLICATION OF T-BUTYLDIMETHYLSILYL ETHERS OF SERINE, THREONINE AND TYROSINE IN PEPTIDE-SYNTHESIS

被引:20
作者
FISCHER, PM
机构
[1] Nycomed Bioreg AS, N-0371 Oslo
关键词
D O I
10.1016/S0040-4039(00)60836-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The utility of Tbdms (t-butyldimethylsilyl) ethers, prepared conveniently in a one-pot procedure from N(alpha)-Fmoc (9-fluorenylmethoxycarbonyl) and N(alpha)-Z (benzyloxycarbonyl) hydroxyamino acids, is demonstrated: peptide bond formation and esterification to 4-alkoxybenzylalcohol resin are achieved readily with these derivatives. The lability of the Tbdms ethers to various reagents enables selective deprotection of the hydroxyl side-chains after peptide chain assembly, desirable, e.g., for phosphorylation or glycosilation.
引用
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页码:7605 / 7608
页数:4
相关论文
共 36 条
[1]   SIMPLE AND CONVENIENT SYNTHESIS OF TERT-BUTYL ETHERS OF FMOC-SERINE, FMOC-THREONINE, AND FMOC-TYROSINE [J].
ADAMSON, JG ;
BLASKOVICH, MA ;
GROENEVELT, H ;
LAJOIE, GA .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (10) :3447-3449
[2]  
ADAMSON JG, 1992, ANAL BIOCHEM, V202, P210
[3]   CONSIDERED AS REAGENTS AND SYNTHETIC METHODS .46. 1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE(DBU) - AN EFFECTIVE BASE FOR THE INTRODUCTION OF TERT-BUTYLDIMETHYLSILYL GROUP IN ORGANIC-COMPOUNDS [J].
AIZPURUA, JM ;
PALOMO, C .
TETRAHEDRON LETTERS, 1985, 26 (04) :475-476
[4]   ANCHORING OF FMOC AMINO-ACID TO 4-ALKOXYBENZYL ALCOHOL RESIN USING A NEW ESTERIFICATION REAGENT [J].
AKAJI, K ;
KURIYAMA, N ;
KIMURA, T ;
FUJIWARA, Y ;
KISO, Y .
TETRAHEDRON LETTERS, 1992, 33 (22) :3177-3180
[5]   A NEW METHOD FOR THE PREPARATION OF TERTIARY BUTYL ETHERS AND ESTERS [J].
ARMSTRONG, A ;
BRACKENRIDGE, I ;
JACKSON, RFW ;
KIRK, JM .
TETRAHEDRON LETTERS, 1988, 29 (20) :2483-2486
[6]   MILD PROCEDURE FOR SOLID-PHASE PEPTIDE-SYNTHESIS - USE OF "FLUORENYLMETHOXYCARBONYLAMINO-ACIDS [J].
ATHERTON, E ;
FOX, H ;
HARKISS, D ;
LOGAN, CJ ;
SHEPPARD, RC ;
WILLIAMS, BJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (13) :537-539
[7]   STABILITY OF FLUORENYLMETHOXYCARBONYLAMINO GROUPS IN PEPTIDE-SYNTHESIS - CLEAVAGE BY HYDROGENOLYSIS AND BY DIPOLAR APROTIC-SOLVENTS [J].
ATHERTON, E ;
BURY, C ;
SHEPPARD, RC ;
WILLIAMS, BJ .
TETRAHEDRON LETTERS, 1979, (32) :3041-3042
[8]   PREPARATION AND USE OF N-FMOC-O-TRT-HYDROXYAMINO ACIDS FOR SOLID-PHASE SYNTHESIS OF PEPTIDES [J].
BARLOS, K ;
GATOS, D ;
KOUTSOGIANNI, S ;
SCHAFER, W ;
STAVROPOULOS, G ;
YAO, WQ .
TETRAHEDRON LETTERS, 1991, 32 (04) :471-474
[9]  
BODANSZKY M, 1984, PRINCIPLES PEPTIDE S, P126
[10]   TERTIARY BUTYL GROUP AS A BLOCKING AGENT FOR HYDROXYL, SULFHYDRYL AND AMIDO FUNCTIONS IN PEPTIDE SYNTHESIS [J].
CALLAHAN, FM ;
PAUL, R ;
ANDERSON, GW ;
ZIMMERMAN, JE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (02) :201-&