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Preparation of tritiated oostatic peptides for study of radioactivity incorporation in flesh fly Neobellieria bullata

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Summary.

A series of insect oostatic peptides containing 3,4-dehydroproline in the C-terminal part or inside of the peptide chain was synthesized and tritiated by addition of 3H2 to double bond of 3,4-dehydroproline residue. 3H-label was introduced also into tyrosine residue of oostatic tetra- and pentapeptides by isotopic exchange of benzyl β-hydrogens. In this way, three types of tritiated peptides were prepared, different in the radiolabeled amino acid position: [3H] Tyr-Asp-Pro-Ala-OH, H-Tyr-Asp-[3H] Pro-Ala-OH, [3H] Tyr-Asp-Pro-Ala-Pro-OH, H-Tyr-Asp-[3H] Pro-Ala-Pro-OH, H-Tyr-Asp-Pro-Ala-[3H] Pro-OH, H-Tyr-Asp-Pro-Ala-Pro5-[3H] Pro-OH and H-Asp-[3H] Pro-OH. These peptides made possible a highly sensitive comparative study on radioactivity incorporation into head and ovaries of the flesh fly Neobellieria bullata, which revealed this process to proceed differently. The reasons of the found differences are discussed.

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Abbreviations

The nomenclature and symbols of amino acids follow the Recommendations of IUPAC/IUB Joint Commission on Biochemical Nomenclature. Eur J Biochem (1984) 138: 9–37.:

Additional abbreviations include:

AA:

amino acid analysis

AcOH:

acetic acid

Boc:

tert-butoxycarbonyl

BrZ:

2-bromobenzyloxycarbonyl

DCC:

N,N′-dicyclohexylcarbodiimide

DCM:

dichloromethane

DIEA:

N,N-diisopropylethylamine

DMA:

N,N-dimethylacetamide

DMF:

N,N-dimethylformamide

EDT:

ethane-1, 2-dithiol

EtOAc:

ethyl acetate

FAB MS:

fast atom bombardment mass spectrometry

Fmoc:

(fluoren-1-yl-methoxy)carbonyl

HOBt:

1-hydroxybenzotriazole

OBzl:

benzyl ester

OMe:

methyl ester

OSu:

succinimide ester

PE:

light petroleum

tBu:

tert-butyl

TFA:

trifluoroacetic acid

TFE:

trifluoroethanol

TFMSA:

trifluoromethane sulfonic acid

TIS:

tri-isopropylsilane

TOTU:

O-cyanoethoxycarbonylmethylidene amino-1,1,3,3-tetramethyl-uronium tetrafluoroborate

TPTU:

O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate

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Authors and Affiliations

  1. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague, Czech Republic

    J. Hlaváček & R. Tykva

  2. 1st Medical Faculty, Charles University, Prague, Czech Republic

    B. Černý

  3. Institute of Entomology, Academy of Sciences of the Czech Republic, České Budějovice, Czech Republic

    B. Bennettová

  4. Institute of Experimental Botany, Academy of Sciences of the Czech Republic, Prague, Czech Republic

    J. Holík

Authors
  1. J. Hlaváček
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  2. B. Černý
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  3. B. Bennettová
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  4. J. Holík
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  5. R. Tykva
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Hlaváček, J., Černý, B., Bennettová, B. et al. Preparation of tritiated oostatic peptides for study of radioactivity incorporation in flesh fly Neobellieria bullata . Amino Acids 33, 489–497 (2007). https://doi.org/10.1007/s00726-006-0406-y

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