SYNTHESIS OF N-BOC-ALPHA-AMINO ACIDS WITH NUCLEOBASE RESIDUES AS BUILDING-BLOCKS FOR THE PREPARATION OF CHIRAL PNA (PEPTIDIC NUCLEIC-ACIDS)

被引：47

作者：

LENZI, A

REGINATO, G

TADDEI, M

机构：

[1] UNIV FLORENCE,DIPARTIMENTO CHIM ORGAN UGO SCHIFF,I-50121 FLORENCE,ITALY

[2] CNR,CTR CHIM COMPOSTI ETEROCICLICI & LORO APPLICAZ,I-50121 FLORENCE,ITALY

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 10期

关键词：

D O I：

10.1016/0040-4039(95)00052-E

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Boc-Glutamic acid alpha-benzyl ester was transformed into 4-bromo-2-(tert-butoxycarbonylamino)-butyric acid benzyl ester using the Barton-Crich protocol. This bromo derivative undergoes nucleophilic substitution with nucleobases to give optically active N-Boc-4-adeninbutyrine (Boc-Aby), N-Boc-4-thyminbutyrine (Boc-Tby), N-Boc-4-guaninbutyrine (Boc-Gby) or N-Boc-4-cytosinbutyrine (Boc-Cby), useful building blocks for the synthesis of chiral peptidic nucleic acids (PNA).

引用

页码：1713 / 1716

页数：4

共 17 条

[11] IMPROVED EFFICIENCY AND SELECTIVITY IN PEPTIDE-SYNTHESIS - USE OF TRIETHYLSILANE AS A CARBOCATION SCAVENGER IN DEPROTECTION OF TERT-BUTYL ESTERS AND TERT-BUTOXYCARBONYL-PROTECTED SITES
MEHTA, A
JAOUHARI, R
BENSON, TJ
DOUGLAS, KT
[J]. TETRAHEDRON LETTERS, 1992, 33 (37) : 5441 - 5444
[12] MEIER C, 1992, ANGEW CHEM INT EDIT, V31, P1008, DOI 10.1002/anie.199210081
[13] SEQUENCE-SELECTIVE RECOGNITION OF DNA BY STRAND DISPLACEMENT WITH A THYMINE-SUBSTITUTED POLYAMIDE
NIELSEN, PE
EGHOLM, M
BERG, RH
BUCHARDT, O
[J]. SCIENCE, 1991, 254 (5037) : 1497 - 1500
[14] SEQUENCE SPECIFIC-INHIBITION OF DNA RESTRICTION ENZYME CLEAVAGE BY PNA
NIELSEN, PE
EGHOLM, M
BERG, RH
BUCHARDT, O
[J]. NUCLEIC ACIDS RESEARCH, 1993, 21 (02) : 197 - 200
[15] UNCONVENTIONAL NUCLEOTIDE ANALOGUES .2. SYNTHESIS OF ADENYL ANALOGUE OF WILLARDIINE
NOLLET, AJH
PANDIT, UK
[J]. TETRAHEDRON, 1969, 25 (24) : 5983 - &
[16] UNCONVENTIONAL NUCLEOTIDE ANALOGUES .1. N9-PURINYL ALPHA-AMINO ACIDS
NOLLET, AJH
HUTING, CM
PANDIT, UK
[J]. TETRAHEDRON, 1969, 25 (24) : 5971 - &
[17] SINGLE-BASE PAIR MUTATION ANALYSIS BY PNA DIRECTED PCR CLAMPING
ORUM, H
NIELSEN, PE
EGHOLM, M
BERG, RH
BUCHARDT, O
STANLEY, C
[J]. NUCLEIC ACIDS RESEARCH, 1993, 21 (23) : 5332 - 5336

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