c o n d e n s a z io n e r - x h + h o - a r - x - a + h o ......fig. 29.26c cleavage of the c—n...

R-XH + HO-A R-X-A + H 2 O X = NH, A = -CO-R peptidasi, lactamasi, collagenasi X = O, A = -CO-R esterasi X = O, A = PO 3 2- fosfatasi, nucleasi condensazione idrolisi Zn 2+ - Substrato +

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Page 1: c o n d e n s a z io n e R - X H + H O - A R - X - A + H O ......Fig. 29.26c Cleavage of the C—N bond Glu-270 His-196 Arg-145 C02- HO Tyr-248 NH His-69 Glu-72 Arg-127 (c) Schematic

R-XH + HO-A R-X-A + H2O

X = NH, A = -CO-R peptidasi, lactamasi, collagenasi

X = O, A = -CO-R esterasi

X = O, A = PO32-

fosfatasi, nucleasi

condensazione

idrolisi

Zn2+ -

Substrato+

Page 2: c o n d e n s a z io n e R - X H + H O - A R - X - A + H O ......Fig. 29.26c Cleavage of the C—N bond Glu-270 His-196 Arg-145 C02- HO Tyr-248 NH His-69 Glu-72 Arg-127 (c) Schematic

Anidrasi carbonica

30 kDa, 259 a.a.

k ≈ 10–1 s–1 → 106 s–1

Page 3: c o n d e n s a z io n e R - X H + H O - A R - X - A + H O ......Fig. 29.26c Cleavage of the C—N bond Glu-270 His-196 Arg-145 C02- HO Tyr-248 NH His-69 Glu-72 Arg-127 (c) Schematic

Sito catalitico della anidrasi carbonica

C OO

- 2+ -

acido di Lewis

base di Lewis

Page 4: c o n d e n s a z io n e R - X H + H O - A R - X - A + H O ......Fig. 29.26c Cleavage of the C—N bond Glu-270 His-196 Arg-145 C02- HO Tyr-248 NH His-69 Glu-72 Arg-127 (c) Schematic

Ciclo catalitico della anidrasi carbonica

Rate limiting

Page 5: c o n d e n s a z io n e R - X H + H O - A R - X - A + H O ......Fig. 29.26c Cleavage of the C—N bond Glu-270 His-196 Arg-145 C02- HO Tyr-248 NH His-69 Glu-72 Arg-127 (c) Schematic

Regione idrofilica

Regione idrofobica

Page 6: c o n d e n s a z io n e R - X H + H O - A R - X - A + H O ......Fig. 29.26c Cleavage of the C—N bond Glu-270 His-196 Arg-145 C02- HO Tyr-248 NH His-69 Glu-72 Arg-127 (c) Schematic

34 kDa, 300 a.a.

Carbossipeptidasi A (CPD A)

idrolisi di amminoacidi C-terminali

k ≈ 10–11 s–1 → 104 s–1

Page 7: c o n d e n s a z io n e R - X H + H O - A R - X - A + H O ......Fig. 29.26c Cleavage of the C—N bond Glu-270 His-196 Arg-145 C02- HO Tyr-248 NH His-69 Glu-72 Arg-127 (c) Schematic

Siti attivi di carbossipeptidasi

Carbossipeptidasi A (CPD A, bovino) Carbossipeptidasi G2 (CPG2, batterio)

Page 8: c o n d e n s a z io n e R - X H + H O - A R - X - A + H O ......Fig. 29.26c Cleavage of the C—N bond Glu-270 His-196 Arg-145 C02- HO Tyr-248 NH His-69 Glu-72 Arg-127 (c) Schematic

Posizionamento del substrato vicino al sito attivo della CPA

Page 9: c o n d e n s a z io n e R - X H + H O - A R - X - A + H O ......Fig. 29.26c Cleavage of the C—N bond Glu-270 His-196 Arg-145 C02- HO Tyr-248 NH His-69 Glu-72 Arg-127 (c) Schematic

Attivazione dell’acqua e suo attacco nucleofilo

Page 10: c o n d e n s a z io n e R - X H + H O - A R - X - A + H O ......Fig. 29.26c Cleavage of the C—N bond Glu-270 His-196 Arg-145 C02- HO Tyr-248 NH His-69 Glu-72 Arg-127 (c) Schematic

Rottura del legame peptidico C-N

Page 11: c o n d e n s a z io n e R - X H + H O - A R - X - A + H O ......Fig. 29.26c Cleavage of the C—N bond Glu-270 His-196 Arg-145 C02- HO Tyr-248 NH His-69 Glu-72 Arg-127 (c) Schematic

Trasferimento di un protone con formazione di NH3+ e del carbossilato

Page 12: c o n d e n s a z io n e R - X H + H O - A R - X - A + H O ......Fig. 29.26c Cleavage of the C—N bond Glu-270 His-196 Arg-145 C02- HO Tyr-248 NH His-69 Glu-72 Arg-127 (c) Schematic

Matrix Metalloproteinases (MMPs) +

Tissue Inhibitors of MetalloProteinases (TIMPs)

= Zn

= Ca

Page 13: c o n d e n s a z io n e R - X H + H O - A R - X - A + H O ......Fig. 29.26c Cleavage of the C—N bond Glu-270 His-196 Arg-145 C02- HO Tyr-248 NH His-69 Glu-72 Arg-127 (c) Schematic

Processo metastatico favorito da MMP

Page 14: c o n d e n s a z io n e R - X H + H O - A R - X - A + H O ......Fig. 29.26c Cleavage of the C—N bond Glu-270 His-196 Arg-145 C02- HO Tyr-248 NH His-69 Glu-72 Arg-127 (c) Schematic

Cromatina e Nucleosomi

Page 15: c o n d e n s a z io n e R - X H + H O - A R - X - A + H O ......Fig. 29.26c Cleavage of the C—N bond Glu-270 His-196 Arg-145 C02- HO Tyr-248 NH His-69 Glu-72 Arg-127 (c) Schematic

Page 16: c o n d e n s a z io n e R - X H + H O - A R - X - A + H O ......Fig. 29.26c Cleavage of the C—N bond Glu-270 His-196 Arg-145 C02- HO Tyr-248 NH His-69 Glu-72 Arg-127 (c) Schematic

Sito attivo di HDAC8

Lisina acetilata

Aspartati

Page 17: c o n d e n s a z io n e R - X H + H O - A R - X - A + H O ......Fig. 29.26c Cleavage of the C—N bond Glu-270 His-196 Arg-145 C02- HO Tyr-248 NH His-69 Glu-72 Arg-127 (c) Schematic

HDAC Inhibitors (HDACi)

agenti antitumorali (modulazione epigenetica del DNA)

Zolinza®

Page 18: c o n d e n s a z io n e R - X H + H O - A R - X - A + H O ......Fig. 29.26c Cleavage of the C—N bond Glu-270 His-196 Arg-145 C02- HO Tyr-248 NH His-69 Glu-72 Arg-127 (c) Schematic

Zinc fingers

gene regulatory proteins e transcription factors

a-elica b-sheet

Page 19: c o n d e n s a z io n e R - X H + H O - A R - X - A + H O ......Fig. 29.26c Cleavage of the C—N bond Glu-270 His-196 Arg-145 C02- HO Tyr-248 NH His-69 Glu-72 Arg-127 (c) Schematic

a-elica

b-sheet

Page 20: c o n d e n s a z io n e R - X H + H O - A R - X - A + H O ......Fig. 29.26c Cleavage of the C—N bond Glu-270 His-196 Arg-145 C02- HO Tyr-248 NH His-69 Glu-72 Arg-127 (c) Schematic

Interazione di zinc-fingers con DNA

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