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- Title
Synthesis of peptide-cellulose conjugate mediated by a soluble cellulose derivative having β-Ala esters (II): conjugates with O-phospho- l-serine-containing peptides.
- Authors
Devarayan, Kesavan; Hachisu, Masakazu; Araki, Jun; Ohkawa, Kousaku
- Abstract
A synthetic route is described here for novel peptide-cellulose conjugates containing O-phospho- l-serine. First, Boc-Ser(POPh) and the related dipeptides, Boc-Ser(POPh)-Asp(OBzl) and Boc-Asp(OBzl)-Ser(POPh), were synthesized by adopting the phosphoryl-protection strategy. The condensation reaction between the α-carboxyl group of the protected Boc-Ser(POPh) and the β-amino groups of β-Ala-Cellulose using isobutyl chloroformate and N-methylmorpholine yielded the product conjugate, N-[Boc-Ser(POPh)]- β-Ala-Cellulose. The degree of substitution of Boc-Ser(POPh) towards the β-amino groups of β-Ala-Cellulose was estimated as DS = 0.75 (maximum, 1.0). Similar reactions between β-Ala-Cellulose and two kinds of protected dipeptides, Boc-Asp(OBzl)-Ser(POPh) and Boc-Ser(POPh)-Asp(OBzl), gave the corresponding conjugates, and the DS was estimated to be 0.95 and 0.69, respectively. The phenyl, benzyl, and Boc groups were removed in one-pot using the PtO catalyst in 50 % trifluoroacetic acid/acetic acid. The P-NMR and UV-Visible spectra indicated the complete deprotection without any observable elimination of the phosphorylated peptides.
- Subjects
CELLULOSE; GLUCANS; AMINO acids; RADICALS (Chemistry); ORGANIC compounds
- Publication
Cellulose, 2013, Vol 20, Issue 1, p365
- ISSN
0969-0239
- Publication type
Article
- DOI
10.1007/s10570-012-9822-1