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Volumn 59, Issue 14, 2003, Pages 2423-2434

Synthesis of bridged sugar amino acids: A new entry into conformationally locked δ- and ε-amino acids

Author keywords

Conformationally restricted; Leu enkephaline; Peptide isoster; Sugar amino acid

Indexed keywords

AMINO ACID DERIVATIVE; BRIDGED COMPOUND; CARBENOID; FORMALDEHYDE; LEUCINE ENKEPHALIN DERIVATIVE; OXETANE DERIVATIVE; RIBOSE; SUGAR;

EID: 0037474623     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00288-6     Document Type: Article
Times cited : (38)

References (48)
  • 5
    • 0015511563 scopus 로고
    • For the definition of north and south confomations see:
    • For the definition of north and south confomations see: Altona C., Sudaralingam M. J. Am. Chem. Soc. 94:1972;8205.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 8205
    • Altona, C.1    Sudaralingam, M.2
  • 36
    • 85031196961 scopus 로고    scopus 로고
    • 6-benzoyl-2′,3′-O-isopropylideneadenosine-5 ′-aldehyde (see Ref. 10d)
    • 6-benzoyl-2′,3′-O-isopropylideneadenosine-5 ′-aldehyde (see Ref. 10d).
  • 37
    • 85031208578 scopus 로고    scopus 로고
    • 1d in the ring closure of 4′-(p-toluenesulfonyl)oxymethyluridine. They ascribed this selectivity for the formation of a 4-membered ring to the predominant S-puckering of the ribose ring, which locates the 3′-OH in close proximity to the 4′-carbon center
    • 1d in the ring closure of 4′-(p-toluenesulfonyl)oxymethyluridine. They ascribed this selectivity for the formation of a 4-membered ring to the predominant S-puckering of the ribose ring, which locates the 3′-OH in close proximity to the 4′-carbon center.
  • 38
    • 85031198890 scopus 로고    scopus 로고
    • The chemical shift of H4 shifted from 5.06 ppm (21) to 5.31 ppm (38), while the chemical shift of H3 shifted from 3.98 ppm (21) to 4.80 ppm (38) (see Section 4)
    • The chemical shift of H4 shifted from 5.06 ppm (21) to 5.31 ppm (38), while the chemical shift of H3 shifted from 3.98 ppm (21) to 4.80 ppm (38) (see Section 4).
  • 41
    • 85031195008 scopus 로고    scopus 로고
    • 3P and Boc-ON prior to the substitution of the mesyl with NaCN the major product that was isolated did not correspond to the desired Boc-protected amine adduct 40, but appeared to be the tricyclic compound 41. Apparently the intermolecular attack of the intermediate iminophosphorane on the mesyl protected primary hydroxyl proceeds faster than the intramolecular reaction with Boc-ON
    • 3P and Boc-ON prior to the substitution of the mesyl with NaCN the major product that was isolated did not correspond to the desired Boc-protected amine adduct 40, but appeared to be the tricyclic compound 41. Apparently the intermolecular attack of the intermediate iminophosphorane on the mesyl protected primary hydroxyl proceeds faster than the intramolecular reaction with Boc-ON.
  • 42
    • 85031206416 scopus 로고    scopus 로고
    • 3 also resulted in partial cleavage of the TBDPS group
    • 3 also resulted in partial cleavage of the TBDPS group.
  • 44
    • 85031201916 scopus 로고    scopus 로고
    • The chemical shift of H4 shifted from 5.02 ppm (32) to 5.29 ppm (39), while the chemical shift of H3 shifted from 3.09 ppm (32) to 4.92 ppm (39) (see Section 4)
    • The chemical shift of H4 shifted from 5.02 ppm (32) to 5.29 ppm (39), while the chemical shift of H3 shifted from 3.09 ppm (32) to 4.92 ppm (39) (see Section 4).
  • 48
    • 85031195426 scopus 로고    scopus 로고
    • 2,3 coupling constant of BSAA 2 could not be determined due to signal overlap
    • 2,3 coupling constant of BSAA 2 could not be determined due to signal overlap.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.