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Application of the disulfide trapping approach to explain the antiparallel assembly of dimeric rabbit uteroglobin: A preliminary study using short peptide models

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Summary

The spontaneous air oxidation of the peptides H-GICPRFAHVIENLL-NH2 and Ac-LPQTTRENIMKLTEKIVKSPLCM-OH, whose sequences correspond to the helicoidal fragments 1–14 and 48–70 of the monomer of rabbit uteroglobin, was studied. While no oxidation products were observed in the absence of trifluoroethanol, the heterodimer was formed selectively in the presence of the structuring agent. Head-to-head and tail-to-tail homodimers were not detected under these conditions. These results suggest that the N- and C-terminal extremes of the monomer of uteroglobin might contain enough structural information to govern dimerization with a head-tail topology, through a selective helix-to-helix recognition process.

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Abbreviations

aa:

amino acid

Boc:

tert-butoxycarbonyl

Bom:

benzyloxymethyl

cHex:

cyclohexyl

DCM:

dichloromethane

DIEA:

diisopropylethylamine

DIPCDI:

diisopropylcarbodiimide

DMAP:

dimethylaminopiridine

DMF:

N,N-dimethylformamide

ESMS:

electrospray ionization mass spectrometry

Fmoc:

9-fluorenylmethoxycarbonyl

HOBt:

1-hydroxybenzotriazole

HPLC:

high-performance liquid chromatography

MBHA:

4-methylbenzhydrylamine resin

Meb:

4-methylbenzyl

MPLC:

medium-performance liquid chromatography

Npys:

3-nitro-2-piridinsulfenyl

Pmc:

2,2,5,7,8-pentamethylchroman-6-sulfonyl

Met(O):

methionine sulfoxide

PEG-PS:

polyethylene glycolpolystyrene resin

rt:

room temperature

TFA:

trifluoroacetic acid

TFE:

trifluoroethanol

Tos:

tosyl

tBu:

tert-butyl

Trt:

trityl

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Authors and Affiliations

  1. Departament de Química Orgànica, Universitat de Barcelona, Marti i Franquès 1-11, E-08028, Barcelona, Spain

    Tina Ferrer, Ernesto Nicolás & Ernest Giralt

Authors
  1. Tina Ferrer
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  2. Ernesto Nicolás
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  3. Ernest Giralt
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Ferrer, T., Nicolás, E. & Giralt, E. Application of the disulfide trapping approach to explain the antiparallel assembly of dimeric rabbit uteroglobin: A preliminary study using short peptide models. Lett Pept Sci 6, 165–172 (1999). https://doi.org/10.1007/BF02443632

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  • DOI: https://doi.org/10.1007/BF02443632

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