Exploring the self-assembly of glycopeptides using a diphenylalanine scaffold

Rinat Roytman; Lihi Adler-Abramovich; K. S.Ajish Kumar; Ting Chun Kuan; Chun Cheng Lin; Ehud Gazit; Ashraf Brik

doi:10.1039/c1ob05071k

Exploring the self-assembly of glycopeptides using a diphenylalanine scaffold

Rinat Roytman, Lihi Adler-Abramovich, K. S.Ajish Kumar, Ting Chun Kuan, Chun Cheng Lin, Ehud Gazit, Ashraf Brik

Tel Aviv University, Ben-Gurion University of the Negev

Research output: Contribution to journal › Article › peer-review

Abstract

Diphenylalanine, a key building block for organic nanotechnology, forms discrete, rigid and hollow nanotubes that are assembled spontaneously upon their dilution from organic phase into aqueous solution. Here we report the efficient preparation of several S-linked glycosylated diphenylalanine analogues bearing different monosaccharide, di-saccharide and sialic acid residues. The self-assembly studies revealed that these glycopeptides adopted various structures and glycosylation could be a tool to manipulate the self-assembly process. Moreover, the solubility of these analogues was found to be much greater than diphenylalanine, which could open new applications based on these nanostructures.

Original language	English
Pages (from-to)	5755-5761
Number of pages	7
Journal	Organic and Biomolecular Chemistry
Volume	9
Issue number	16
DOIs	https://doi.org/10.1039/c1ob05071k
State	Published - 21 Aug 2011

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1039/c1ob05071k

Cite this

@article{4678839ecced46d6ae671c14ea4604ac,

title = "Exploring the self-assembly of glycopeptides using a diphenylalanine scaffold",

abstract = "Diphenylalanine, a key building block for organic nanotechnology, forms discrete, rigid and hollow nanotubes that are assembled spontaneously upon their dilution from organic phase into aqueous solution. Here we report the efficient preparation of several S-linked glycosylated diphenylalanine analogues bearing different monosaccharide, di-saccharide and sialic acid residues. The self-assembly studies revealed that these glycopeptides adopted various structures and glycosylation could be a tool to manipulate the self-assembly process. Moreover, the solubility of these analogues was found to be much greater than diphenylalanine, which could open new applications based on these nanostructures.",

author = "Rinat Roytman and Lihi Adler-Abramovich and Kumar, {K. S.Ajish} and Kuan, {Ting Chun} and Lin, {Chun Cheng} and Ehud Gazit and Ashraf Brik",

year = "2011",

month = aug,

day = "21",

doi = "10.1039/c1ob05071k",

language = "الإنجليزيّة",

volume = "9",

pages = "5755--5761",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "16",

}

TY - JOUR

T1 - Exploring the self-assembly of glycopeptides using a diphenylalanine scaffold

AU - Roytman, Rinat

AU - Adler-Abramovich, Lihi

AU - Kumar, K. S.Ajish

AU - Kuan, Ting Chun

AU - Lin, Chun Cheng

AU - Gazit, Ehud

AU - Brik, Ashraf

PY - 2011/8/21

Y1 - 2011/8/21

N2 - Diphenylalanine, a key building block for organic nanotechnology, forms discrete, rigid and hollow nanotubes that are assembled spontaneously upon their dilution from organic phase into aqueous solution. Here we report the efficient preparation of several S-linked glycosylated diphenylalanine analogues bearing different monosaccharide, di-saccharide and sialic acid residues. The self-assembly studies revealed that these glycopeptides adopted various structures and glycosylation could be a tool to manipulate the self-assembly process. Moreover, the solubility of these analogues was found to be much greater than diphenylalanine, which could open new applications based on these nanostructures.

AB - Diphenylalanine, a key building block for organic nanotechnology, forms discrete, rigid and hollow nanotubes that are assembled spontaneously upon their dilution from organic phase into aqueous solution. Here we report the efficient preparation of several S-linked glycosylated diphenylalanine analogues bearing different monosaccharide, di-saccharide and sialic acid residues. The self-assembly studies revealed that these glycopeptides adopted various structures and glycosylation could be a tool to manipulate the self-assembly process. Moreover, the solubility of these analogues was found to be much greater than diphenylalanine, which could open new applications based on these nanostructures.

UR - http://www.scopus.com/inward/record.url?scp=79960987707&partnerID=8YFLogxK

U2 - 10.1039/c1ob05071k

DO - 10.1039/c1ob05071k

M3 - مقالة

C2 - 21720631

SN - 1477-0520

VL - 9

SP - 5755

EP - 5761

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 16

ER -

Exploring the self-assembly of glycopeptides using a diphenylalanine scaffold

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this