ISSN:
0021-8995
Keywords:
Chemistry
;
Polymer and Materials Science
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
,
Mechanical Engineering, Materials Science, Production Engineering, Mining and Metallurgy, Traffic Engineering, Precision Mechanics
,
Physics
Notes:
The propensity of benzyloxycarbonylamide group towards clean and rapid hydrogenolysis was exploited in designing a linker for solid phase peptide synthesis on a copoly(styrene-divinylbenzene) resin support. Hydroxymethyl copoly(styrene-divinylbenzene) on treatment with 4-nitrophenyl chloroformate gave a resin which possessed benzyl 4-nitrophenyl carbonate pendants. These reacted with the α-amino group of Boc-Lys-OMe, resulting in the attachment of the latter through its side chain to the resin by a benzyloxycarbonylamide linkage. This was used to extend the peptide chain from the α-amino end of lysine by Bocmethodology. The peptide was released from the resin through palladium acetate-ammonium formate-based transfer hydrogenolysis. The usefulness of this linker was demonstrated by synthesizing several small peptides terminating in lysine. © 1995 John Wiley & Sons, Inc.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/app.1995.070560912
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