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Metalloproteases peptide synthesis

Mutahi, M., Nittoh, T., Guo, L., Sieburth, S. M. Silicon-based metalloprotease inhibitors synthesis and evaluation of silanol and silanediol peptide analogues as inhibitors of angiotensin-converting enzyme. J. Am. Chem. Soc. 2002,124(25), 7363—7375. [Pg.341]

Metalloproteases and glutamic and aspartic proteases, on the other hand, do not form covalent intermediates, but activate a water molecule that directly attacks the carbonyl carbon of the peptide bond and displaces the amide nitrogen [49]. These enzymes are often the preferred catalysts for thermodynamically controlled coupling (Figure 15.1). An example of a metalloprotease applied for peptide synthesis is thermolysin, which contains a HExxH+E sequence motif that coordinates a zinc ion and a water molecule. Zinc polarizes the carbonyl group and facilitates deprotonation of the... [Pg.399]

The serine, cysteine, and aspartic proteases and the metalloproteases have all been applied in peptide synthesis. Nevertheless, shortcomings still exist and at an industrial scale chemoenzymatic peptide synthesis is certainly not always the preferred method. Since the properties of the catalyst to a large extent determine the feasibility of industrial application, the discovery and engineering of better variants are an intensive field of research. [Pg.402]

The metalloprotease thermolysin has been widely used for peptide synthesis [66,67]. Thermolysin is produced and secreted by the thermophilic bacterium Bacillus thermo-proteolyticus. Catalysis involves water activation by a zinc ion that is coordinated by side chains of two histidines and a glutamate. Thermolysin specificity is defined by its Sr pocket accepting large hydrophobic, polar, and charged residues. In the SI pocket hydrophobic residues are preferred, and Leu > Ala > Phe > Gly is the preference order for the S2 and S2 pockets. This hydrolytic specificity of thermolysin is reflected in its synthetic specificity. [Pg.407]

Peptides with C-terminal phosphonates, initially reported to have antibacterial properties, have also been found to possess inhibitory properties toward serine proteases)28 The synthesis of peptide phosphonates (Section 15.1.8) usually requires protection of the phos-phonic moiety as a diester, followed by selective deprotection in the final stage. The importance of peptide thiols (Section 15.1.9) is exemplified by captopril, an orally active angiotensin converting enzyme inhibitor used as a treatment for hypertension)29 These peptide thiols are prepared by the reaction of sulfanylalkanoyl amino acids with a-amino esters followed by deprotection of carboxy and sulfanyl groups. Other peptide thiols have been reported to be inhibitors of zinc metalloproteases, collagenases, and aminopeptidases. [Pg.3]

The understanding of the mechanistic principles underlying the catalytic chemistry of metalloproteases has been applied in the design and synthesis of a number of biomimetic metal complexes that ftinction as artificial proteases. These complexes include mononuclear wateractivating complexes, and multinuclear complexes that combine carboxyl terminal recognition, peptide carbonyl polarization, and water nucleophile activation fimctions. ... [Pg.5505]

Ottl J, Battistuta R, Pieper M, Tschesche H, Bode W, Kiihn K, Moroder L. Design and synthesis of heterotrimeric collagen peptides with a built-in cystine-knot. Models for collagen catabolism by matrix-metalloproteases. FEBS. Lett. 1996 398 31-36. [Pg.270]

The solution-phase synthesis and resolution of new phosphinopeptidic building blocks containing a triple bond and their involvement in 1,3-dipolar cycloaddition with a variety of in j// -prepared nitrile oxides allowed the diastereoselective preparation of a novel class of isoxazole-containing phosphinic peptides 619. Inhibition assays of some of these peptides revealed their behavior as very potent inhibitors of metalloproteases, outmatching previously reported phosphinic peptides in terms of potency <2003CEJ2079>. [Pg.470]


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See also in sourсe #XX -- [ Pg.395 ]

See also in sourсe #XX -- [ Pg.6 , Pg.395 ]

See also in sourсe #XX -- [ Pg.395 ]




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