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Three-dimensional arrangement of sugar residues along helical polypeptide backbone. 2. Synthesis of periodic N-glycosylated peptides by polymerization of tripeptide active esters containing alpha,alpha-disubstituted amino acid.

Abstract：

:New type of N-glycosylated peptides having periodic sequence of -[X-Gln(beta-D-GlcNAc)-Aib]- [X = L-Glu(OMe), L-Lys(Ac), L-Ala; Aib = alpha-aminoisobutyric acid] were synthesized by polymerization of glycosylated tripeptides with an active ester methods using Cl(-+)H(3)N-L-Glu(OMe)-Gln[beta-D-GlcNAc(Ac)(3)]-Aib-ONp (Np=p-nitrophenyl) (13a), Cl(-+)H(3)N-L-Lys(Ac)-Gln[beta-D-GlcNAc(Ac)(3)]-Aib-ONp (13b), and Cl(-+)H(3)N-L-Ala-Gln[beta-D-GlcNAc(Ac)(3)]-Aib-ONp (13c) as the monomers. Polymerizable glycosylated tripeptides were prepared by stepwise N,N-dicyclohexylcarbodiimide (DCC)/1-hydroxybenzotriazole (HOBt) method. Polymerizations of 13a-c were initiated by triethylamine and proceeded in DMSO at 50 degrees C for 5 days in the presence of 1-hydroxy-7-azabenzotriazole (HOAt) as the activator (conversions were 25-75%). The glycopeptides were deacetylated by hydrazine monohydrate in methanol to afford periodic glycopeptides 14 (12-27 residues) without racemization (yield, 35-89%). CD spectra in methanol, trifluoroethanol, and water of deacetylated glycopolymers 14a, 14b, and 14c showed double minima (206 and 222 nm) of negative Cotton effect indicating that N-glycoside (N-acetyl-d-glucosamine) was arranged three-dimensionally along the alpha-helical peptides in water as well as in organic protic solvents. The helix content depends on the solvent, peptide sequence, and spacer between peptide backbone and sugar. Interaction of the glycopeptides with wheat germ agglutinin (WGA) lectin was investigated by fluorescence measurement.

journal_name

Biomacromolecules

journal_title

Biomacromolecules

authors

Takasu A,Horikoshi S,Hirabayashi T

doi

10.1021/bm0502563

keywords:

subject

Has Abstract

pub_date

2005-07-01 00:00:00

pages

2334-42

issue

4

eissn

1525-7797

issn

1526-4602

journal_volume

6

pub_type

杂志文章

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