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Enzyme-specific activation versus leaving group ability.

de Beer RJ, Bögels B, Schaftenaar G, Zarzycka B, Quaedflieg PJ, van Delft FL, Nabuurs SB, Rutjes FP - Chembiochem (2012)

Bottom Line: Enzyme-specific activation and the substrate mimetics strategy are effective ways to circumvent the limited substrate recognition often encountered in protease-catalyzed peptide synthesis.A key structural element in both approaches is the guanidinophenyl (OGp) ester, which enables important interactions for affinity and recognition by the enzyme--at least, this is usually the explanation given for its successful application.In this study we show that leaving group ability is of equal or even greater importance.

View Article: PubMed Central - PubMed

Affiliation: Institute for Molecules and Materials, Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands.

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Structures of OGp analogues. OGp: p-guanidinophenyl ester; O3G: 3-guanidinopropyl ester; NGp: p-guanidinobenzyl amide; OAb: p-amidinobenzyl ester; OGb: p-guanidinobenzyl ester.
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fig05: Structures of OGp analogues. OGp: p-guanidinophenyl ester; O3G: 3-guanidinopropyl ester; NGp: p-guanidinobenzyl amide; OAb: p-amidinobenzyl ester; OGb: p-guanidinobenzyl ester.

Mentions: The analogues were designed in such a way that they closely resemble OGp in structure, although the leaving group character was varied considerably (Scheme 1).


Enzyme-specific activation versus leaving group ability.

de Beer RJ, Bögels B, Schaftenaar G, Zarzycka B, Quaedflieg PJ, van Delft FL, Nabuurs SB, Rutjes FP - Chembiochem (2012)

Structures of OGp analogues. OGp: p-guanidinophenyl ester; O3G: 3-guanidinopropyl ester; NGp: p-guanidinobenzyl amide; OAb: p-amidinobenzyl ester; OGb: p-guanidinobenzyl ester.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3569868&req=5

fig05: Structures of OGp analogues. OGp: p-guanidinophenyl ester; O3G: 3-guanidinopropyl ester; NGp: p-guanidinobenzyl amide; OAb: p-amidinobenzyl ester; OGb: p-guanidinobenzyl ester.
Mentions: The analogues were designed in such a way that they closely resemble OGp in structure, although the leaving group character was varied considerably (Scheme 1).

Bottom Line: Enzyme-specific activation and the substrate mimetics strategy are effective ways to circumvent the limited substrate recognition often encountered in protease-catalyzed peptide synthesis.A key structural element in both approaches is the guanidinophenyl (OGp) ester, which enables important interactions for affinity and recognition by the enzyme--at least, this is usually the explanation given for its successful application.In this study we show that leaving group ability is of equal or even greater importance.

View Article: PubMed Central - PubMed

Affiliation: Institute for Molecules and Materials, Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands.

Show MeSH