INFRARED SPECTROSCOPIC STUDIES OF VANCOMYCIN AND ITS INTERACTIONS WITH N-ACETYL-D-ALA-D-ALA AND N,N'-DIACETYL-L-LYS-D-ALA-D-ALA

被引:4
|
作者
SALTER, CJ [1 ]
MITCHELL, RC [1 ]
DRAKE, AF [1 ]
机构
[1] UNIV LONDON,BIRKBECK COLL,DEPT CHEM,LONDON WC1H 0PP,ENGLAND
关键词
D O I
10.1039/p29950002203
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The infrared (IR) spectrum of vancomycin, in D2O solution, has been assigned by recording spectra at different pD values and by comparing them with the spectrum in H2O at pH 5. The effects of self-association on the spectrum of vancomycin at pD 5 have also been investigated. Details of underlying components of the broad bands in the spectra were revealed using resolution enhancement and second derivatives. The IR spectra of two peptide models, N-Ac-D-Ala-D-Ala and N,N'-Ac-2-L-Lys-D-Ala-D-Ala, have also been assigned in D2O solution. The interactions of these peptides with vancomycin, in pD 5 solution, have been studied by infrared spectroscopy and the above assignments used to interpret the observed spectral changes; the solubilities of the vancomycin-peptide complexes at pD 5 were determined to facilitate these studies. The IR spectra of the complexes show substantial increases in intensity of a component at about 1588 cm(-1). Using C-13 labelled N-Ac-D-Ala-D-Ala this was found to be due to the asymmetric stretch of the carboxylate group of the peptide, showing that this group undergoes a substantial perturbation on binding to vancomycin.
引用
收藏
页码:2203 / 2211
页数:9
相关论文
共 50 条
  • [1] IMMUNOCHEMISTRY OF (L-ALA-D-GLU-L-LYS-D-ALA-GLY)N - ANTIBODIES OF RESTRICTED SPECIFICITY
    ZEIGER, AR
    MAURER, PH
    [J]. IMMUNOCHEMISTRY, 1974, 11 (09): : 555 - 563
  • [2] Tight binding of a dimeric derivative of vancomycin with dimeric L-Lys-D-Ala-D-Ala
    Rao, JH
    Whitesides, GM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (43) : 10286 - 10290
  • [3] Crystallization and preliminary X-ray crystallographic analysis of a vancomycin-N-acetyl-D-Ala-D-Ala complex
    McPhail, D
    Cooper, A
    Freer, A
    [J]. ACTA CRYSTALLOGRAPHICA SECTION D-BIOLOGICAL CRYSTALLOGRAPHY, 1999, 55 : 534 - 535
  • [4] Conformational studies of resin-bound vancomycin and the complex of vancomycin and Ac2-L-Lys-D-Ala-D-Ala
    Yao, NH
    He, WY
    Lam, KS
    Liu, G
    [J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2005, 7 (01): : 123 - 129
  • [5] A N-15 NMR-STUDY OF INTERMOLECULAR INTERACTIONS BETWEEN VANCOMYCIN AND AC-D-ALA-D-ALA
    HAWKES, GE
    MOLINARI, H
    SINGH, S
    LIAN, LY
    [J]. JOURNAL OF MAGNETIC RESONANCE, 1987, 74 (01): : 188 - 192
  • [6] THEORETICAL CONFORMATIONAL-ANALYSIS ON N-ACETYL-N'-METHYLAMIDE OF L-ALA-D-ALA DIPEPTIDE
    OKA, M
    NAKAJIMA, A
    [J]. POLYMER JOURNAL, 1984, 16 (07) : 553 - 558
  • [7] STRUCTURE OF VANCOMYCIN AND A VANCOMYCIN D-ALA-D-ALA COMPLEX IN SOLUTION
    MOLINARI, H
    PASTORE, A
    LIAN, LY
    HAWKES, GE
    SALES, K
    [J]. BIOCHEMISTRY, 1990, 29 (09) : 2271 - 2277
  • [8] IMMUNOCHEMISTRY OF (L-ALA-D-GLU-L-LYS-D-ALA-GLY)N .2. RABBIT ANTIBODIES OF RESTRICTED HETEROGENEITY
    ZEIGER, AR
    MAURER, PH
    [J]. ZEITSCHRIFT FUR IMMUNITATS-FORSCHUNG EXPERIMENTELLE UND KLINISCHE IMMUNOLOGIE, 1975, 149 (2-4): : 151 - 156
  • [9] Vancomycin resistance: Modeling backbone variants with D-Ala-D-Ala and D-Ala-D-Lac peptides
    Leung, Siegfried S. F.
    Tirado-Rives, Julian
    Jorgensen, William L.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (04) : 1236 - 1239
  • [10] KINETIC STUDIES ON D-ALA-D-ALA SYNTHETASE
    NEUHAUS, FC
    [J]. FEDERATION PROCEEDINGS, 1962, 21 (02) : 229 - &