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Strategies for the highly efficient synthesis of erythropoietin N‐glycopeptide hydrazides
Author(s) -
Hessefort Markus,
Hessefort Hendrik,
Seeleithner Simone,
Gross Angelina,
Lott Marie,
Rau David,
Kern Laura,
Unverzagt Carlo
Publication year - 2021
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.3283
Subject(s) - glycopeptide , chemistry , erythropoietin , peptide , cleavage (geology) , chromatography , solid phase synthesis , peptide synthesis , combinatorial chemistry , high performance liquid chromatography , biochemistry , medicine , fracture (geology) , antibiotics , geotechnical engineering , engineering
A convergent synthesis for erythropoietin (EPO) 1‐28 N‐glycopeptide hydrazides was developed. In this approach, EPO 1‐28 peptides were synthesized on the solid phase and converted to C‐terminal hydrazides after cleavage from the resin. After selective deprotection of the Asp24 side chain, the desired glycosylamine was coupled by pseudoproline‐assisted Lansbury aspartylation. Although the initial yields of the EPO 1‐28 glycopeptides were satisfactory, they could be markedly improved by increasing the purity of the peptide using a reversed‐phase high‐performance liquid chromatography (RP‐HPLC) purification of the protected peptide.