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Volumn 7, Issue 9, 1997, Pages 1119-1122

Polyamide based nucleic acid analogs synthesis of δ-amino acids with nucleic acid bases bearing side chains

Author keywords

[No Author keywords available]

Indexed keywords

CYTOSINE DERIVATIVE; NUCLEIC ACID BASE; PEPTIDE NUCLEIC ACID;

EID: 0343852708     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00172-8     Document Type: Article
Times cited : (19)

References (27)
  • 1
    • 0030056240 scopus 로고    scopus 로고
    • For recent reviews cf., e. g.: a. Crooke, S. T. Med. Res. Rev. 1996, 16. 319 - 344.
    • (1996) Med. Res. Rev. , vol.16 , pp. 319-344
    • Crooke, S.T.1
  • 10
    • 0028918024 scopus 로고
    • c. Lenzi, A.; Reginato, G.; Taddei, M. Tetrahedron Lett. 1995, 36. 1713 - 1716; Lenzi, A.; Reginato. G.: Taddei. M.; Trifilieff, E. Tetrahedron Lett. 1995, 36, 1717-1718
    • (1995) Tetrahedron Lett. , vol.36 , pp. 1713-1716
    • Lenzi, A.1    Reginato, G.2    Taddei, M.3
  • 15
    • 0342829571 scopus 로고
    • For a review on earlier attempts to construct polyamide based nucleic acid analogs see: Jones, S. A. Int. J. Biol. Macromolecules 1979, 1, 194 - 206.
    • (1979) Int. J. Biol. Macromolecules , vol.1 , pp. 194-206
    • Jones, S.A.1
  • 16
    • 0343264463 scopus 로고    scopus 로고
    • The term "nucleoamino acid" is meant to signify amino acids with side chains bearing nucleic acid bases
    • The term "nucleoamino acid" is meant to signify amino acids with side chains bearing nucleic acid bases.
  • 17
    • 0000720794 scopus 로고
    • Modelling studies on polyamide based nucleic acid analogs containing building blocks related to II (all carbon chain) have been reported: Weller, D. D.; Daly. D. T.; Olson, W. K.; Summerton, J. E. J. Org. Chem. 1991, 52, 6000-6006. The synthesis of a thymine derivative related to III (all carbon chain) has recently been described: Savithri, D.; Leumann, C.; Scheffold. R. Helv. Chim. Acta 1996, 79, 288 - 294.
    • (1991) J. Org. Chem. , vol.52 , pp. 6000-6006
    • Weller, D.D.1    Daly, D.T.2    Olson, W.K.3    Summerton, J.E.4
  • 18
    • 0030058035 scopus 로고    scopus 로고
    • Modelling studies on polyamide based nucleic acid analogs containing building blocks related to II (all carbon chain) have been reported: Weller, D. D.; Daly. D. T.; Olson, W. K.; Summerton, J. E. J. Org. Chem. 1991, 52, 6000-6006. The synthesis of a thymine derivative related to III (all carbon chain) has recently been described: Savithri, D.; Leumann, C.; Scheffold. R. Helv. Chim. Acta 1996, 79, 288 - 294.
    • (1996) Helv. Chim. Acta , vol.79 , pp. 288-294
    • Savithri, D.1    Leumann, C.2    Scheffold, R.3
  • 19
    • 0025193588 scopus 로고
    • Breton, P.: Monsigny. M.: Mayer, R. Int. J. Peptide Protein Res. 1990, 35, 346 - 351. The optical purity of 1 was determined by chiral analytical HPLC. Using (S)-2-(benzyloxymethyl)-2-aminoethanol as a reference (prepared from Nα-BOC-DSer(OBn)-OH in analogy to 1), the ee of 1 was shown to be >99%. As none of the subsequent steps in the synthesis of 7, 10, 13, and 13A is conceivably accompanied by epimerization of the chiral center α to the amino group, the optical purity of 1 will also be reflected in these final products.
    • (1990) Int. J. Peptide Protein Res. , vol.35 , pp. 346-351
    • Breton, P.1    Monsigny, M.2    Mayer, R.3
  • 25
    • 0343264462 scopus 로고    scopus 로고
    • note
    • 1H-NMR spectroscopy indicated de's of > 99%. Chemical Equation Presented.
  • 27
    • 85077981913 scopus 로고
    • b. G. Kokotos, Synthesis 1990, 299 - 301. It has been shown that this method proceeds with retention of optical activity (ref. 14b).With regard to the optical purity of 19 and 20 cf. ref. 8.
    • (1990) Synthesis , pp. 299-301
    • Kokotos, G.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.