Premium
Advances in ultra‐high load polymer‐supported peptide synthesis with phenolic supports: 1. A selectively‐labile c‐terminal spacer group for use with a base‐mediated n‐terminal deprotection strategy and fmoc amino acids
Author(s) -
Butwell Francis G.W.,
Haws Edmund J.,
Epton Roger
Publication year - 1988
Publication title -
makromolekulare chemie. macromolecular symposia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.257
H-Index - 76
eISSN - 1521-3900
pISSN - 0258-0322
DOI - 10.1002/masy.19880190105
Subject(s) - peptide , hydroxymethyl , chemistry , polymer , acrylamide , peptide synthesis , matrix (chemical analysis) , protecting group , amino acid , base (topology) , group (periodic table) , terminal (telecommunication) , high performance liquid chromatography , polymer chemistry , combinatorial chemistry , organic chemistry , chromatography , copolymer , biochemistry , mathematical analysis , telecommunications , alkyl , mathematics , computer science
Crosslinked poly(N‐[2‐(4‐hydroxphenyl)ethyl]‐acrylamide) has been modified by conversion of each pendant 4‐hydroxyphenyl group to its 2‐(4‐hydroxymethyl‐phenoxy)ethanoyl‐L‐prolyl ester. This provides a spacer group which makes the polymer matrix suitable for solid (gel) phase peptide synthesis with Fmoc amino acids at ultra‐high load (2.2 mmol g −1 of spacer‐modified support). The selectively labile linkages incorporated in the spacer group provide for peptide detachment by either mild acidolysis or hydrazinolysis. The products of hydrazinolysis of intermediate and final peptide‐matrix assemblies are amenable to analysis by high‐pressure liquid chromatography (HPLC).