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Volumn 60, Issue 10, 2004, Pages 2235-2246

Synthesis of novel analogs of aromatic peptide nucleic acids (APNAs) with modified conformational and electrostatic properties

Author keywords

Novel aromatic peptide nucleic acid monomers; PNA APNA triplexes with DNA and RNA

Indexed keywords

2 (TERT BUTOXYCARBONYLAMINOBENZYLAMINO)ACETIC ACID BENZYL ESTER; 2 AMINO 3 [[TERT BUTOXYCARBONYLMETHYL[2 (5 METHYL 2,4 DIOXO 3,4 DIHYDRO 2H PYRIMIDIN 1 YL)ACETYL]AMINO]METHYL]BENZOIC ACID METHYL ESTER; 3 (2 TERT BUTOXYCARBONYLAMINOPHENYLAMINO)PROPIONIC ACID METHYL ESTER; 3 BROMOMETHYL 2 NITROBENZOIC ACID METHYL ESTER; 3 METHYL 2 NITROBENZOIC ACID METHYL ESTER; 3 [(2 TERT BUTOXYCARBONYLAMINOPHENYL)[2 (5 METHYL 2,4 DIOXO 3,4 DIHYDRO 2H PYRIMIDIN 1 YL)ACETYL]AMINO]PROPIONIC ACID METHYL ESTER; 3 [(TERT BUTOXYCARBONYLMETHYLAMINO)METHYL] 2 NITROBENZOIC ACID METHYL ESTER; 3 [[(TERT BUTOXYCARBONYLMETHYL[2 (5 METHYL 2,4 DIOXO 3,4 DIHYDRO 2H PYRIMIDIN 1 YL)ACETYL]AMINO]METHYL] 2 NITROBENZOIC ACID METHYL ESTER; AROMATIC PEPTIDE NUCLEIC ACID; DNA; PEPTIDE NUCLEIC ACID; RNA; UNCLASSIFIED DRUG; [(2 TERT BUTOXYCARBONYLAMINOBENZYL)[2 (5 METHYL 2,4 DIOXO 3,4 DIHYDRO 2H PYRIMIDIN 1 YL)ACETYL]AMINO]ACETIC ACID BENZYL ESTER; [2 [(2,3 DIHYDROXYPROPYL)[2 (5 METHYL 2,4 DIOXO 3,4 DIHYDRO 2H PYRIMIDIN 1 YL)ACETYL]AMINO]BENZYL]CARBAMIC ACID TERT BUTYL ESTER; [2 [[2 (5 METHYL 2,4 DIOXO 3,4 DIHYDRO 2H PYRIMIDIN 1 YL)ACETYL](2 OXOETHYL)AMINO]BENZYL]CARBAMIC ACID TERT BUTYL ESTER; [2 [[2 (5 METHYL 2,4 DIOXO 3,4 DIHYDRO 2H PYRIMIDIN 1 YL)ACETYL]AMINO]BENZYL]CARBAMIC ACID TERT BUTYL ESTER; [[2 TERT BUTOXYCARBONYLAMINOMETHYL)PHENYL][2 (5 METHYL 2,4 DIOXO 3,4 DIHYDRO 2H PYRIMIDIN 1 YL)ACETYL]AMINO]ACETIC ACID;

EID: 1242351225     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.01.026     Document Type: Article
Times cited : (11)

References (69)
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    • Job plots were used to confirm the 2:1 stoichiometry of the complexes formed as previously described: (a) Ref. 19.
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    • Ab inition minimization (at the HF/6-31G* level of theory) was carried out on model compounds corresponding to the core backbone structure of monomers 1 , 4 and 5 , respectively. These calculations provided unambiguous evidence of the order of polarity of these analogs (most polar 5 ≫ 4 > 1 least polar); a significant increase in polarity is expected to correlate with an increase in the solubility of that compound in aqueous media. In addition, we observed the anticipated differences in the retention time for each compound on a C18 reversed phase HPLC column. Finally, although the exact solubility of each compound was not determined, qualitatively it was clearly apparent that the new APNA monomers 4 and 5 were more soluble in polar solvents than the first generation analog 1 .
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    • Modifications to the synthesis cycles for Fmoc-synthesis of PNA oligomers were as previously described. See Ref. 20b.
    • Modifications to the synthesis cycles for Fmoc-synthesis of PNA oligomers were as previously described. See Ref. 20b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.