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The Synthesis of Fully Boe-Protected Insulin Derivatives by Use of Boc-Azide - 1,1,3,3-Tetramethylguanidine - 1,2,4-Triazole as an Effective Acylating System. - A Simple and Sensitive Fluorescence Test for Determining the Degree of N-Substitution

D. Keglević ; Tracer Laboratory, »Ruder Boskovic« Institute, POB 1016, 41001 Zagreb
S. Vuksan ; Tracer Laboratory, »Ruder Boskovic« Institute, POB 1016, 41001 Zagreb
B. Mulac ; Tracer Laboratory, »Ruder Boskovic« Institute, POB 1016, 41001 Zagreb
B. Ladešić ; Tracer Laboratory, »Ruder Boskovic« Institute, POB 1016, 41001 Zagreb
S. Iskrić ; Tracer Laboratory, »Ruder Boskovic« Institute, POB 1016, 41001 Zagreb
S. Kveder ; Tracer Laboratory, »Ruder Boskovic« Institute, POB 1016, 41001 Zagreb

Sažetak

Acylation of desoctapeptide-(1323-3°) -insulin pentamethyl ester
(II), insulin arid insulin 'hexamethyl ester was carried out with
Boc-azide in dimethylformamide in the presence of 1,1,3,3-tetramethylguanidine
as a base and 1,2,4-triazole as an activator to give
very homogeneous di-Boc-desoctapeptide-(B23- 30)-insulin p~ntamethyl
ester (III), tri-Boc-insulin (IV) and tri-Boc-insulin hexamethyl
ester (V), respectively, in high yield (> 900/o). The degree of substitution
of the products was assayed by a simple and sensitive test,
based on the fluorescence reaction with primary amines, and expressed
as the fluorescence intensity relative to that produced by an
equimolar amount of free insulin. A comparison of the fluorescence
intensities of III and IV prepared under various conditions indicates
that (a) the Boc-azide - 1,1,3,3-tetramethylguanidine - 1,2,4-triazole
combination is more effectiv.e than the Boc-azide - imidazole and
Boc-azide - triethylamine acylating systems, and (b) the presence
of 1,2,4-triazole is·essential for the acylating efficiency of the system
employed.

Ključne riječi

Hrčak ID:

195967

URI

https://hrcak.srce.hr/195967

Datum izdavanja:

26.9.1978.

Posjeta: 895 *