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Angewandte Chemie International Edition in English
Volumn 14, Issue 6, 1975, Pages 375-386
Three‐Dimensional Structure of the Actinomycins
Author keywords

Actinomycins; Antibiotics; Conformation analysis; X ray structure analysis
Indexed keywords

ANTINEOPLASTIC AGENT; DACTINOMYCIN; LACTONE; PEPTIDE FRAGMENT;
EID: 0016418839     PISSN: 05700833     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.197503751     Document Type: Article
Times cited : (49)
References (80)
  • 29
    • 84982385314 scopus 로고    scopus 로고
    • Chloroform dissolves all the actinomycins, peptide lactones, and their precursors equally well and is currently the best solvent for comparative studies. “Moist” deuteriochloroform: the solution to be measured is shaken for a short time with a few drops of deuterium oxide and then centrifuged.
  • 31
    • 84982367591 scopus 로고    scopus 로고
    • As the concentration of 2 is increased the original monomer spectrum becomes overlaid by another which finally reaches equal intensity. The signals of the latter spectrum are mostly at higher field values and should be derived from the inner protons of the dimer that are situated between the two peptide rings and are thus additionally shielded.
  • 32
    • 84982379376 scopus 로고    scopus 로고
    • Habilitationsschrift. Universität Göttingen 1972.
    • Lackner, H.1
  • 35
    • 84982378787 scopus 로고    scopus 로고
    • * see Fig. 13.
  • 38
    • 84982356381 scopus 로고    scopus 로고
    • 13C‐NMR measurements.
  • 48
    • 84982383801 scopus 로고    scopus 로고
    • IR measurements were of little value for deciding the cis/trans‐assignment; the optical rotations of the “A” and the “C” conformer differ considerably.
  • 54
    • 84982385119 scopus 로고    scopus 로고
    • The NH → ND exchange, for example, is almost as slow as in the “C”‐conformer of 2.
  • 57
    • 84982355168 scopus 로고    scopus 로고
    • 2N hydrogen bond (Fig. 12) in dissolved actinomycin D 1 [32, 42] explains some of the findings, but this is not in accord with other NMR data. particularly those for actinomycin derivatives such as (7g).
  • 62
    • 84982379472 scopus 로고    scopus 로고
    • Steric hindrance is, of course, only one of the reasons for the inactivity of these actinomycins. It is relevant, for example, that the three‐dimensional relationships no longer permit the formation of hydrogen bridges between the guanosine groups of the DNA and the threonine group of the now enantiomeric peptide chains [14–16]: cf. Section 7.
  • 63
    • 84982376009 scopus 로고    scopus 로고
    • Similar remarks apply to seco‐actinomycins (one peptide ring opened between sarcosine and methylvaline). The conformations of actinomycin acids (5c) are very complex and hitherto unknown.
  • 64
    • 84982383155 scopus 로고    scopus 로고
    • 3 signals for the (α)‐and (β)‐peptide chains are assigned on the basis of spectra of (α,β)‐specifically N‐methyl‐deuteriated actinomycin acid lactones [26].
  • 70
    • 84982385704 scopus 로고    scopus 로고
    • 13C‐NMR spectra of the pentapeptide lactones, actinomycins, and deuterioactinomycins.
  • 71
    • 84982385721 scopus 로고    scopus 로고
    • 13C‐NMR spectra.
  • 72
    • 84982353944 scopus 로고    scopus 로고
    • Some actinomycins contain sarcosine in place of L‐proline as amino acid 3. They have the configurational sequence I.D.—I. and also assume the characteristic three‐dimensional structure, even if in apparently somewhat more labile form.
  • 73
    • 84982384825 scopus 로고    scopus 로고
    • A = adenine, T = thymine, G = guanine, C = cytosine.
  • 75
    • 84982346653 scopus 로고    scopus 로고
    • As the water cools from 25 to 0–4°C the solubility of the actinomycins increases by 2–3 powers of ten:, Diplomarbeit. Universität Göttingen 1961.
    • Schulmeyer, K.H.1

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.