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Chemical synthesis of15N-labeled analogues of zervamicin IIB

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Abstract

Analogues of 16-membered peptide antibiotic zervamicin IIB with the Gln3 and Gln11 residues15N-labeled at the Cα-atoms were synthesized by coupling the antibiotic segments (1–4), (5–9), and (10–16). In turn, these were prepared by a stepwise chain elongation in solution starting from theirC-termini using benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP) as an activating agent. The sterically hindered 2-aminoisobutyric acid was introduced by the BOP-dimethylaminopyridine system with the preactivation of the carboxyl component. The segment condensation was performed with the use of the 6-trifluoromethylbenzotriazol-1-yloxy-tris(pyrrolidino)phosphonium hexafluorophosphate activating reagent. The homogeneity of the resulting zervamicin analogues was confirmed by HPLC, and their structures were proved by NMR spectroscopy and FAB mass spectrometry.

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Abbreviations

Aib:

2-aminoisobutyric acid residue

BOP:

benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

DIPEA:

diisopropylethylamine

DMAP:

4-dimethylaminopyridine

Fmoc:

9-fluorenylmethyloxycarbonyl

HOBt(CF3):

1-hydroxy-6-trifluoromethylbenzotriazole

Hyp:

hydroxyproline residue

Iva:

isovaline residue

Phl:

phenylalaninol residue

PyBOP(CF3):

6-trifluoromethylbenzotriazol-1-yloxy-tris(pyrrolidino)phosphonium hexafluorophosphate

PyBrop:

bromotris(pyrrolidino)phosphonium hexafluorophosphate

TFA:

trifluoroacetic acid

TIPS:

triisopropylsilane

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Authors and Affiliations

  1. Lomonosov State Academy of Fine Chemical Technology, pr. Vernadskogo 86, 117571, Moscow, Russia

    W. H. Rimawi, An. A. Ogrel & V. I. Shvets

  2. Leiden University, The Netherlands

    J. Raap

Authors
  1. W. H. Rimawi
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  2. An. A. Ogrel
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  3. J. Raap
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  4. V. I. Shvets
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Correspondence to W. H. Rimawi.

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Rimawi, W.H., Ogrel, A.A., Raap, J. et al. Chemical synthesis of15N-labeled analogues of zervamicin IIB. Russ J Bioorg Chem 26, 725–733 (2000). https://doi.org/10.1007/BF02759625

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  • DOI: https://doi.org/10.1007/BF02759625

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