Vasoactive intestinal peptide is an amino acceptor and donor substrate for tissue transglutaminase (TGase) in vitro. This peptide contains a single glutamine residue, Gln(16) which was identified as the amino acceptor substrate. Different gamma(glutamyl(16))amine derivatives of vasoactive intestinal peptide were synthesized enzymatically in vitro. The modification is very fast when compared with that of many native substrates of TGase. The analogs 1,3-diaminopropane, putrescine, cadaverine, spermidine, spermine, glycine ethyl ester and mono-dansylcadaverine of the peptide were purified by high-performance liquid chromatography on a reverse-phase column and were analyzed by electrospray mass spectrometry, When amines were absent in the assay mixture as an external amino donor, lysine residue occurring in the peptide was an effective amino donor site for TGase. Only one of the three lysine residues of vasoactive intestinal peptide, namely Lys(21), was demonstrated to be involved in both inter- and intramolecular cross-link formation.

Enzymatic synthesis of vasoactive intestinal peptide analogs by transglutaminase / C., Esposito; A., Cozzolino; Mariniello, Loredana; P., Stiuso; S., De Maria; S., Metafora; Ferranti, Pasquale; M., Carteni Farina. - In: JOURNAL OF PEPTIDE RESEARCH. - ISSN 1397-002X. - STAMPA. - 53:6(1999), pp. 626-632.

Enzymatic synthesis of vasoactive intestinal peptide analogs by transglutaminase

MARINIELLO, LOREDANA;FERRANTI, PASQUALE;
1999

Abstract

Vasoactive intestinal peptide is an amino acceptor and donor substrate for tissue transglutaminase (TGase) in vitro. This peptide contains a single glutamine residue, Gln(16) which was identified as the amino acceptor substrate. Different gamma(glutamyl(16))amine derivatives of vasoactive intestinal peptide were synthesized enzymatically in vitro. The modification is very fast when compared with that of many native substrates of TGase. The analogs 1,3-diaminopropane, putrescine, cadaverine, spermidine, spermine, glycine ethyl ester and mono-dansylcadaverine of the peptide were purified by high-performance liquid chromatography on a reverse-phase column and were analyzed by electrospray mass spectrometry, When amines were absent in the assay mixture as an external amino donor, lysine residue occurring in the peptide was an effective amino donor site for TGase. Only one of the three lysine residues of vasoactive intestinal peptide, namely Lys(21), was demonstrated to be involved in both inter- and intramolecular cross-link formation.
1999
Enzymatic synthesis of vasoactive intestinal peptide analogs by transglutaminase / C., Esposito; A., Cozzolino; Mariniello, Loredana; P., Stiuso; S., De Maria; S., Metafora; Ferranti, Pasquale; M., Carteni Farina. - In: JOURNAL OF PEPTIDE RESEARCH. - ISSN 1397-002X. - STAMPA. - 53:6(1999), pp. 626-632.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11588/457451
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