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Subtilisin Carlsberg in complex with sodium dodecyl sulfate is an effective catalyst for the solid phase segment coupling of peptides on polyvinyl alcohol cryogel

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Abstract

Subtilisin Carlsberg (SC) was shown to catalyze the solid phase segment coupling of peptides in complex with sodium dodecyl sulfate (SDS) in an organic medium on Aminosilochrom and polyvinyl alcohol (PVA) cryogel activated with glutaraldehyde or divinylsulfone. Diamines of different lengths with a general formula NH2-(CH2) n -NH2 (n = 2, 4, and 6) were used as spacers between the PVA cryogel and the peptide. A model reaction of enzymatic attachment of the Dnp-Ala-Ala-Leu-OMe tripeptide to the PVA cryogel was carried out by treatment with the SDS-SC complex in a mixture of anhydrous ethanol and DMSO (7 : 3, v/v) using a tenfold excess of the carboxyl component. The molar enzyme-substrate ratio was 1 : 88. The effect of the method of matrix activation, length of a spacer, and reaction time on the coupling efficiency was studied. Hexamethylenediamine was found to be the most effective spacer for the enzymatic coupling on the PVA cryogel activated with glutaraldehyde (the reaction proceeded with the highest yield of 60%). The reaction efficiency was considerably lower in the case of ethylenediamine and tetramethylenediamine (10 and 15%, respectively). The best results were obtained on the PVA cryogel activated by divinylsulfone with hexamethylenediamine as a spacer. A two-step condensation of tripeptides was carried out on this support. The second step of condensation was shown to proceed better (in 85% yield) in comparison with the first step (37% yield).

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Abbreviations

AOT:

aerosol of ESS

Boc:

tert-butyloxycarbonyl

Dnp:

2,4-dinitrophenyl

DVS:

divinylsulfone

EDA:

ethylenediamine

ESS:

sodium bis(2-ethylhexyl)sulfosuccinate

GA:

glutaraldehyde

HMDA:

hexamethylenediamine

PEGA:

polyethylene glycol-acrylamide

PVA:

polyvinyl alcohol

TMDA:

tetramethylenediamine

SC:

subtilisin Carlsberg

SDS-SC:

complex of SC with sodium dodecyl sulfate

Z:

benzyloxycarbonyl

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Correspondence to I. Yu. Filippova.

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Original Russian Text © O.M. Anikina, E.N. Lysogorskaya, E.S. Oksenoit, V.I. Losinskii, I.Yu. Filippova, 2008, published in Bioorganicheskaya Khimiya, 2008, Vol. 34, No. 3, pp. 365–370.

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Anikina, O.M., Lysogorskaya, E.N., Oksenoit, E.S. et al. Subtilisin Carlsberg in complex with sodium dodecyl sulfate is an effective catalyst for the solid phase segment coupling of peptides on polyvinyl alcohol cryogel. Russ J Bioorg Chem 34, 329–333 (2008). https://doi.org/10.1134/S1068162008030138

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  • DOI: https://doi.org/10.1134/S1068162008030138

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