Self-assembling nanowires from a linear l,d-peptide conjugated to the dextran end group

Luca Raganato; Alessandra Del Giudice; Anita Ceccucci; Fabio Sciubba; Stefano Casciardi; Simona Sennato; Anita Scipioni; Giancarlo Masci

doi:10.1016/j.ijbiomac.2022.03.050

Self-assembling nanowires from a linear l,d-peptide conjugated to the dextran end group

Int J Biol Macromol. 2022 May 15:207:656-665. doi: 10.1016/j.ijbiomac.2022.03.050. Epub 2022 Mar 12.

Authors

Luca Raganato¹, Alessandra Del Giudice¹, Anita Ceccucci², Fabio Sciubba³, Stefano Casciardi⁴, Simona Sennato⁵, Anita Scipioni⁶, Giancarlo Masci⁷

Affiliations

¹ Department of Chemistry, Sapienza Università di Roma, P.le A. Moro, 5, I-00185 Rome, Italy.
² Department of Industrial, Electronic and Mechanical Engineering, Roma Tre University, via Vito Volterra 62, Roma, Italy.
³ Department of Environmental biology, Sapienza University of Rome, P.le Aldo Moro 5, 00185 Rome, Italy; NMR-based Metabolomics Laboratory (NMLab), Sapienza University of Rome, P.le Aldo Moro 5, 00185 Rome, Italy.
⁴ National Institute for Insurance Against Accidents at Work (INAIL Research), Department of Occupational and Environmental Medicine, Epidemiology and Hygiene, Rome, Italy.
⁵ Institute for Complex Systems, National Research Council (ISC-CNR), Sede Sapienza and Department of Physics, Sapienza Università di Roma, P.le A. Moro, 2, 00185, Rome, Italy.
⁶ Department of Chemistry, Sapienza Università di Roma, P.le A. Moro, 5, I-00185 Rome, Italy. Electronic address: anita.scipioni@uniroma1.it.
⁷ Department of Chemistry, Sapienza Università di Roma, P.le A. Moro, 5, I-00185 Rome, Italy. Electronic address: giancarlo.masci@uniroma1.it.

PMID: 35292281
DOI: 10.1016/j.ijbiomac.2022.03.050

Abstract

Preparation and characterization of a block-like l,d-octapeptide-dextran conjugate DEX₂₉-(l-Val-d-Val)₄ self-assembling into nanowire structures is reported. The conjugate was prepared by solid phase click-chemistry on an alkyne group N-terminus functionalized peptide with a regularly alternating enantiomeric sequence. Low molecular weight dextran (X_n = 29) with moderately low dispersity (1.30) was prepared by controlled acid hydrolysis and dialysis with selected cut-off and functionalized with an azido group on the reducing end by reductive amination. The strong hydrogen bonds and hydrophobic interactions of the (l-Val-d-Val)₄ linear peptide drive the conjugate to self-assemble into long (0.1-1 μm) nanowires. To our knowledge, this is the first example of a peptide-polysaccharide conjugate that can self-assemble into a nanowire architecture.

Keywords: Click-chemistry; Dextran; Nanowires; Self-assembling; l,d linear peptide with regularly alternating enantiomeric sequence.

MeSH terms

Alkynes / chemistry
Dextrans*
Nanowires*
Peptides / chemistry
Renal Dialysis

Substances

Alkynes
Dextrans
Peptides