@article { ISI:000295890100006, title = {Bicyclic amino acid-carbohydrate-conjugates as conformationally restricted hydroxyethylamine (HEA) transition-state isosteres}, journal = {Organic \& Biomolecular Chemistry}, volume = {9}, number = {21}, year = {2011}, month = {SEP}, pages = {7300-7302}, publisher = {ROYAL SOC CHEMISTRY}, address = {THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND}, abstract = {

This communication describes a general synthetic route to bicyclic amino acid-carbohydrate-conjugates, which would be useful as conformationally restricted hydroxyethylamine (HEA) transition-state isosteres. The synthesis was achieved in 12 steps starting from D-glucose. The striking features of this system are the bicyclic rigid core displaying an a-amino acid side chain and hydroxyethylamine moiety - both of which would be potentially important for receptor interactions, leading to various biomedical responses, as described in the literature. Crystal structure investigation suggested extensive intermolecular hydrogen-bonding interactions in this system, involving the backbone amide and hydroxyl groups.

}, issn = {1477-0520}, doi = {10.1039/c1ob06215h}, author = {Kale, Sangram S. and Chavan, Sanjay T. and Sabharwal, Sushma G. and Puranik, Vedavati G. and Sanjayan, Gangadhar J.} } @article {49445, title = {Block copolymer self-assembly: exploitation of hydrogen bonding for nanoparticle morphology control via incorporation of triazine based comonomers by RAFT polymerization}, journal = {Small}, volume = {20}, year = {2024}, month = {OCT}, pages = {2401129}, type = {Article}, abstract = {

Synthesis of polymeric nanoparticles of controlled non-spherical morphology is of profound interest for a wide variety of potential applications. Self-assembly of amphiphilic diblock copolymers is an attractive bottom-up approach to prepare such nanoparticles. In the present work, RAFT polymerization is employed to synthesize a variety of poly(N,N-dimethylacrylamide)-b-poly[butyl acrylate-stat-GCB] copolymers, where GCB represents vinyl monomer containing triazine based Janus guanine-cytosine nucleobase motifs featuring multiple hydrogen bonding arrays. Hydrogen bonding between the hydrophobic blocks exert significant influence on the morphology of the resulting nanoparticles self-assembled in water. The Janus feature of the GCB moieties makes it possible to use a single polymer type in self-assembly, unlike previous work exploiting, e.g., thymine-containing polymer and adenine-containing polymer. Moreover, the strength of the hydrogen bonding interactions enables use of a low molar fraction of GCB units, thereby rendering it possible to use the present approach for copolymers based on common vinyl monomers for the development of advanced nanomaterials.

}, doi = { https://doi.org/10.1002/smll.202401129}, author = {Haque, Farah and Thompson, Steven W. and Ishizuka, Fumi and Kuchel, Rhiannon P. and Singh, Dharmendra and Sanjayan, Gangadhar J. and Zetterlund, Per B.} }