Synthesis and coupling reactions of alpha,alpha-dialkylated amino acids with nucleobase side chains

被引:4
作者
Azumaya, I
Aebi, R
Kubik, S
Rebek, J
机构
[1] Department of Chemistry, Massachusetts Inst. of Technology, Cambridge
关键词
D O I
10.1073/pnas.92.26.12013
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
Several di- and tripeptides containing protected purine (adenine) and pyrimidine (thymine) residues on their side chains were synthesized. The parent amino acids are alpha,alpha-dialkylated in a symmetrical manner. An effective coupling procedure was developed for these sterically hindered amino acids: the fluoren-9-ylmethyloxycarbonyl-protected amino acid was dehydrated to its oxazolinone form, which was coupled in good yields with amino esters in hot tetrachloroethane.
引用
收藏
页码:12013 / 12016
页数:4
相关论文
共 20 条
[11]   SELF-ASSEMBLING ORGANIC NANOTUBES BASED ON A CYCLIC PEPTIDE ARCHITECTURE [J].
GHADIRI, MR ;
GRANJA, JR ;
MILLIGAN, RA ;
MCREE, DE ;
KHAZANOVICH, N .
NATURE, 1993, 366 (6453) :324-327
[12]  
GOODMAN M, 1992, INT J PEPT PROT RES, V40, P282
[13]   SYNTHESIS OF ALPHA,ALPHA-DIALKYLATED AMINO-ACIDS WITH ADENINE OR THYMINE RESIDUES - A NEW MILD AND FACILE HYDROLYSIS OF HYDANTOINS [J].
KUBIK, S ;
MEISSNER, RS ;
REBEK, J .
TETRAHEDRON LETTERS, 1994, 35 (36) :6635-6638
[14]   CYCLO(D-PRO-L-PRO-D-PRO-L-PRO) - STRUCTURAL-PROPERTIES AND CIS TRANS ISOMERIZATION OF THE CYCLOTETRAPEPTIDE BACKBONE [J].
MASTLE, W ;
WEBER, T ;
THEWALT, U ;
ROTHE, M .
BIOPOLYMERS, 1989, 28 (01) :161-174
[15]   STRUCTURAL VERSATILITY OF PEPTIDES FROM C-ALPHA,ALPHA-DISUBSTITUTED GLYCINES - SYNTHESIS, CHARACTERIZATION, AND SOLUTION CONFORMATIONAL-ANALYSIS OF HOMOPEPTIDES FROM C-ALPHA-METHYL-C-ALPHA-BENZYLGLYCINE, [(ALPHA-ME)PHE]N(1) [J].
PANTANO, M ;
FORMAGGIO, F ;
CRISMA, M ;
BONORA, GM ;
MAMMI, S ;
PEGGION, E ;
TONIOLO, C ;
BOESTEN, WHJ ;
BROXTERMAN, QB ;
SCHOEMAKER, HE ;
KAMPHUIS, J .
MACROMOLECULES, 1993, 26 (08) :1980-1984
[16]   SYNTHETIC REPLICATORS AND EXTRABIOTIC CHEMISTRY [J].
PARK, TK ;
FENG, Q ;
REBEK, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (12) :4529-4532
[17]  
SRIKRISHNAN T, 1982, INT J PEPT PROT RES, V19, P103
[18]   BIOACTIVE AND MODEL PEPTIDES CHARACTERIZED BY THE HELICOGENIC (ALPHA-ME)PHE RESIDUE [J].
TONIOLO, C ;
FORMAGGIO, F ;
CRISMA, M ;
VALLE, G ;
BOESTEN, WHJ ;
SCHOEMAKER, HE ;
KAMPHUIS, J ;
TEMUSSI, PA ;
BECKER, EL ;
PRECIGOUX, G .
TETRAHEDRON, 1993, 49 (17) :3641-3653
[19]   FMOC AMINO-ACID FLUORIDES - CONVENIENT REAGENTS FOR THE SOLID-PHASE ASSEMBLY OF PEPTIDES INCORPORATING STERICALLY HINDERED RESIDUES [J].
WENSCHUH, H ;
BEYERMANN, M ;
KRAUSE, E ;
BRUDEL, M ;
WINTER, R ;
SCHUMANN, M ;
CARPINO, LA ;
BIENERT, M .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3275-3280
[20]   SELF-REPLICATING MOLECULES - A 2ND GENERATION [J].
WINTNER, EA ;
CONN, MM ;
REBEK, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (20) :8877-8884