Recognition of Novel Lipopolypeptides with Many Pendent Sugar Residues by Lectin

Abstract

A lipid-polypeptide conjugate (lipo-polypeptide) was obtained by the ring-opening polycondensation of N-epsilon-Z-L-lysine N-carboxyanhydride (NCA) using 3-aminopropyl dioctadecylamine as initiator and subsequent deprotection. Maltose lactone was coupled with the lipo-polypeptide to give novel amphiphiles which carried many maltoamide residues as pendent groups. The sugar group-carrying amphiphiles incorporated in phospholipid liposomes were recognized by a lectin from Canavalia ensiformis (Con A), which was proven by the increase in turbidity of the liposome suspension after mixing with the lectin. The recognition was largely affected by the degree of polymerization of lysine residues and the surface density of the amphiphile in the liposomes. The association constant (K(ass)) of Con A with maltoamide residues on the liposome was much larger than those for small molecular weight sugars due to the "cluster effect".

Mannose-decorated cyclodextrin vesicles: The interplay of multivalency and surface density in lectin–carbohydrate recognition

“…The surface coverage of guests 2 and 4 is gradually reduced by substitution with “inert” guest 6 . Concentrations: [5] = 20 μM, [2] = 0–5.0 μM: [4] = 0–5.0 μM, [6] = 0–10 μM; [ConA] = 0.1 mg/mL. (B) Maximal aggregation depending on surface coverage of guest 2 or 4 .…”

Synthesis and characterization of poly(vinyl amine)‐based amphiphilic comb‐like dextran glycopolymers by a two‐step method

“…2‐Propanol was used as the solvent and chain transfer reagent to produce PVAm with relatively low molecular weight, as reported previously 18. Briefly, poly( N ‐vinylformamide) (PNVF) was first obtained at 65 °C after 4 h of free radical polymerization of N ‐vinylformamide (2.5 g, 35 mmol) in mixed solvents of formamide/2‐propanol (1:9, v/v), with AIBN (57 mg, 0.35 mmol) as the initiator.…”

“…The postpolymerization grafting method involves making a well‐defined backbone polymer first, and then attaching the saccharide and hydrophobic branches to create the amphiphilic polymer 4, 18. For example, a series of polymeric saccharide surfactants have been synthesized by our group, using a one‐step method by attaching saccharide lactone and alkyl succinimide simultaneously on a poly(vinyl amine) (PVAm) backbone 19, 20.…”

Self-association of zwitterionic polymer–lipid conjugates in water as examined by scattering measurements

“…Since lipids are natural compounds, they have a great advantage in biomedical use (e.g., as drug carriers). In fact, there have been many studies on the properties and functions of biomaterials containing natural or synthetic lipids [8][9][10][11][12]. Furthermore, 2-methacryloyloxyethylphosphorylcholine (MPC), a zwitterionic vinyl monomer analogous to a phosphorylcholine head group of a natural lipid, has been copolymerized with apolar monomers such as n-butyl methacrylate to afford excellent biocompatible properties such as resistance against non-specific protein adsorption, cell adhesion, and thrombus formation [13][14][15].…”