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Volumn 120, Issue 44, 1998, Pages 11297-11303

Preferred conformation of C-lactose at the free and peanut lectin bound states

Author keywords

[No Author keywords available]

Indexed keywords

LACTOSE; LECTIN; METHYL ALPHA C LACTOSIDE; UNCLASSIFIED DRUG;

EID: 0032508934     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja982193k     Document Type: Article
Times cited : (90)

References (48)
  • 2
    • 3643132242 scopus 로고    scopus 로고
    • note
    • The term exo-anomeric conformation is used to describe the conformation of O-or C-glycosidic bond with the glycosidic oxygen or carbon being anti-periplanar to the C.1-C.2 bond.
  • 11
    • 84988099658 scopus 로고
    • All dihedral angles are defined according to the IUPAC Joint Commission on Biochemical Nomenclature (JCBN), symbols for specifying the conformation of polysaccharide chains, 1981 recommendation. Reproduced in Eur. J. Biochem. 1983, 131, 5; φ = O.5′-C.1′-O.4-C.4 and ψ = C.1′-O.4-C.4-C.3.
    • (1983) Eur. J. Biochem. , vol.131 , pp. 5
  • 12
    • 3643055079 scopus 로고    scopus 로고
    • note
    • The single-axial-like interaction of C.2′-O.2′/C.a-H is not included in Table 1 because it exists in all the three staggered conformers A-C.
  • 13
    • 5844327067 scopus 로고
    • With an imaginative six-membered ring including O.5′-C.1′-C.a-C.4 on the conformer C, it is seen that the C.5 and C.6 carbons correspond to the quaternary and primary carbons of the terr-butyl group of tert-butylcyclohexane. Thus, the single-axial-like interaction between the C.1′-H and the C.4-C.5-C.6-C.6-H (or OH) is assumed to be roughly represented by 1/2 of the A-value (4.9 kcal/mol) of terf-butylcyclohexane reported by Manoharan, M.; Eliel, E. L. Tetrahedron Lett. 1984, 25, 3267. The single-axial-like interaction of C.4-C.a-C.1′-C.1′-H/C.6-H is the same type of interaction as this. However, since this interaction involves the same protons as the single-axial-like interaction of C.4-C.5/C.1′-H, the steric destabilization is counted only once.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 3267
    • Manoharan, M.1    Eliel, E.L.2
  • 15
    • 3643088586 scopus 로고    scopus 로고
    • note
    • 5a
  • 22
    • 3643095839 scopus 로고    scopus 로고
    • note
    • 2 are an additional example for this general observation.
  • 23
    • 3643094797 scopus 로고    scopus 로고
    • note
    • 3OD, 7/3) δ 2.37 (H.4) 3.84. (H.1′), 3.9 (H.5′) 3.96 (H.2), 3.99 (H.3′), 4.11 (H.6), 4.17 (H.6′), 4.20 (H.5), 4.21 (H.2′), 4.29 (H.3), 4.34 (H.6), 4.37 (H.6′), 4.40 (H.4′), 5.11 (H.1).
  • 24
    • 3643066626 scopus 로고    scopus 로고
    • note
    • 4 for the conformational study of the aglyconic bond. The synthesis of these substrates and the NOESY spectrum are included in Supporting Information.
  • 27
    • 3643093655 scopus 로고    scopus 로고
    • note
    • 3OD, 7/3) δ 4.02 (H.2), 4.06 (H.5), 4.07 (H.3′), 4.08 (H.5′), 4.15 (H.4), 4.29 (H.6′), 4.35 (H.6), 4.38 (H.6′), 4.4 (H.2′), 4.41 (H.3), 4.43 (H.6), 4.43 (H.4′), 5.0 (H.1′), 5.04 (H.1).
  • 28
    • 3643062426 scopus 로고    scopus 로고
    • For example, see the discussion given in ref 4
    • For example, see the discussion given in ref 4.
    • J. Phys. Chem. A
  • 35
    • 3643086465 scopus 로고    scopus 로고
    • note
    • 24b
  • 36
    • 3643124951 scopus 로고    scopus 로고
    • note
    • 24a
  • 37
    • 3643131215 scopus 로고    scopus 로고
    • note
    • The φ and ψ values given here are averaged over the four subunits of the protein.
  • 38
    • 3643079156 scopus 로고    scopus 로고
    • note
    • 4 searched for the best agreement between experimental and back-calculated NOE distances, resulting in two refined structures with φ = 295°/ψ = 130° and φ = 295°/ψ = 300°.
  • 39
    • 0000667775 scopus 로고
    • The conformation of O-lactose bound to peanut lectin is well compared with the crystal structure (φ = 266°; ψ = 95°) of O-lactose monohydrate: Beevers, C. A.; Hans, N. H. Acta Crystallogr. 1971, B27, 1323-1325.
    • (1971) Acta Crystallogr. , vol.B27 , pp. 1323-1325
    • Beevers, C.A.1    Hans, N.H.2
  • 43
    • 0002444999 scopus 로고
    • Diamond, R., Ramaseshan, S., Venkatesan, K., Eds.; Indian Academy of Sciences: Bangalore
    • Vijayan, M. In Computing in Crystallography; Diamond, R., Ramaseshan, S., Venkatesan, K., Eds.; Indian Academy of Sciences: Bangalore, 1980, 19.01-19.26.
    • (1980) Computing in Crystallography , pp. 1901-1926
    • Vijayan, M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.