Enantioselective binding of α-amino acids at poly(<scp>L</scp>-glutamic acid)-functionalized monolayer surfaces

Higashi, Nobuyuki; Saitou, Maki; Mihara, Taku; Niwa, Masazo

doi:10.1039/c39950002119

Cited by 20 publications

(16 citation statements)

References 10 publications

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“…Recently, Chechik and Stirling 10 and Karpovich and Blanchard 11 have shown that apolar monolayers are easily penetrated by common solvents. Selective recognition of chlorinated solvents, 12 nucleic acids, 3 a -amino acids, 13 and proteins 2,5,14,15 has also been reported. Interlayer binding processes have been demonstrated for v -functionalized monolayers interacting with vapor-phase alkanoic acids, 16±18 liquid crystals, 19 and organophosphonates; 20 but also within the monolayer itself hydrogen-bonding interactions have been observed.…”

Section: Introductionmentioning

confidence: 95%

Adsorption and Ordering of Resorcinare Layers on Planar and Colloidal Gold and the Influence of Surface Modification: A SERS and IRRAS Study

Nissink

Maas

1999

Appl Spectrosc

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Near-infrared surface-enhanced Raman spectroscopy and infrared re¯ection-absorption spectroscopy have been applied to investigate adsorption and ordering processes of resorcin arene cavitands at interfaces. Colloidal gold was applied in the case of NIR-Ram an m easurem ents, and planar gold substrates were used for re¯ection spectroscopy. Selected cavitands substituted on their upper rim with different functionalities were em ployed as probe m olecules. An assignment of vibrational bands is presen ted. Interactions between probe m olecules and substrates are present in all cases. From Raman measurements, it is dif® cult to deduce an orientation of the probe molecule adsorbed onto the gold particle, as the selection rules for SERS cannot be applied straightforwardly. Furtherm ore, an orientation depends on a proper assignment of vibrational bands. Infrared spectroscopy shows that the orientation of the resorcinarene m olecules deposited on a planar gold or gold/m onolayer interface is in¯uenced by the underlying substrate. The directing effect, however, does not extend into the adjoining bulk of the sample layer.

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Section: Introductionmentioning

confidence: 95%

Adsorption and Ordering of Resorcinare Layers on Planar and Colloidal Gold and the Influence of Surface Modification: A SERS and IRRAS Study

Nissink

Maas

1999

Appl Spectrosc

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“…Poly(L-glutamic acid) (PLGA) has been employed as the element of a protein model because of its ease of preparation and its well-defined conformational characteristics in aqueous solutions. PLGA has been modified at the chain end with two long alkyl chains, so as to behave as an amphiphile and then be able to float on water (5)(6)(7)(8)(9).…”

Section: Introductionmentioning

confidence: 99%

Effects of Helical Sense and Macrodipole on Helix Interaction in Poly(glutamic acid) Monolayers at the Air–Water Interface

Higashi

Nishikawa

Koga

et al. 1999

Journal of Colloid and Interface Science

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“…It has been recognized that the specific location of the amino acids yields the molecular recognition domain in the receptor2, 3 and is closely related to the induced signal transfer on and through the biological membrane. It has been reported4–9 that artificial systems composed of an ordered assembly of functional groups show specific binding behavior for some substrates. Stewart et al10 reported on the design and synthesis of a polypeptide with chymotrypsin‐like catalytic activity.…”

Section: Introductionmentioning

confidence: 99%

Substrate-induced formation of a recognition structure in a four-polypeptide-lipid monolayer system

Higuchi

Taguchi

Wright

et al. 2000

J. Polym. Sci. A Polym. Chem.

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Poly(γ‐methyl L‐glutamate)s with Ser, His, Asp, and Glu residues at the amino terminal as the serine protease catalytic site were prepared. The number‐average degree of polymerization of the polypeptides was 51. A dipalmitoylphosphatidylcholine monolayer containing the polypeptides was formed at the air–water interface and was transferred onto gold‐deposited glass plates. The binding of N‐acetyltyrosine ethyl ester, a typical substrate of the serine protease, to the monolayer was characterized by surface plasmon resonance measurements. The four‐polypeptide–lipid monolayer system conditioned on an aqueous solution containing the substrate N‐acetyltyrosine ethyl ester exhibited Langmuir‐type binding of the substrate. Its binding constant of 6.1 × 104 M−1 was about 20 times larger than that observed for a monolayer prepared on pure water. The behavior may have arisen from a substrate‐induced rearrangement of the four kinds of polypeptides in the monolayer, forming a substrate‐binding structure similar to that found in serine protease. © 2000 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 38: 2186–2191, 2000

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Enantioselective binding of α-amino acids at poly(L-glutamic acid)-functionalized monolayer surfaces

Abstract: A poly(L-glutamic acid)-functionalized monolayer 1 has the ability t o capture a-amino acids enantioselectively in aqueous solution due t o a highly assembled structure of the a-helical poly(L-glutamic acid) segments at the monolayer surface.

Cited by 20 publications

References 10 publications

Adsorption and Ordering of Resorcinare Layers on Planar and Colloidal Gold and the Influence of Surface Modification: A SERS and IRRAS Study

Adsorption and Ordering of Resorcinare Layers on Planar and Colloidal Gold and the Influence of Surface Modification: A SERS and IRRAS Study

Effects of Helical Sense and Macrodipole on Helix Interaction in Poly(glutamic acid) Monolayers at the Air–Water Interface

Substrate-induced formation of a recognition structure in a four-polypeptide-lipid monolayer system

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