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Syntheses and conformational studies of poly-β,N-alkyl L-asparagines

✍ Scribed by Tadao Hayakawa; Hiroyuki Yamamoto; Noriko Aoto

Publisher
Wiley (John Wiley & Sons)
Year
1972
Tongue
English
Weight
631 KB
Volume
11
Category
Article
ISSN
0006-3525

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✦ Synopsis

Several &N-alkyl basparagines were prepared from the phthalyl and benzyloxycar-bony1 derivatives. High-molecular-weight poly-&N-benzyl Lasparaghe and poly-&N-(1 )-phenethyl r.-asparagine were prepared from the corresponding N-carboxyanhydrides. From the results obtained by a study of the infrared absorption spectra and the optical rotatory dispersion, poly-8-N-benzyl L-asparagine was found to be a random coil structure in dichloroacetic acid and the optical rotatory dispersion curves gradually changed into the left-handed a-helix structure when chloroform was added to the solution. The coil-to-helix transition was observed in the vicinity of 20% dichloroacetic acid in a dichloroacetic acid-chloroform mixture. Poly-&N-(d), (I), and (d + I, 1: I)*-(1)-phenethyl L-asparagines showed a nearly constant specific rotation in the dichloroacetic acidchloroform solvent system. Poly-&N-(dI)-( 1)-phenethyl L-asparagine caused a gradual folding of the helix a t dichloroacetic acid content of less than 20%. * (d + 2, 1: 1):mixed polymer containing the same weighed poly-p,N-(d) and (Z)-(1)phenethyl L-asparagines.

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