Enantiomer-Differentiating Ability of Cyclo(L-Phe-L-Pro)4 Having a Rigid Skeleton for Phenylalanine Methylester Hydrochloride

The formation constant of the 1 : 1 complex of cyclo(L-Phe-L-Pro)4 (1) with L-PheOMe·HCl was about 13.2 times that of the complex with D-PheOMe·HCl. The 1 : 1 complex of 1 with L-PheOMe·HCl formed three intermolecular hydrogen bonds between Pro2 CO, Phe1 CO and the amino group, and Phe2 NH and the c...

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 45; no. 7; pp. 1202 - 1204
Main Authors ISHIZU, Takashi, NOGUCHI, Shunsaku
Format Journal Article
LanguageEnglish
Published Tokyo The Pharmaceutical Society of Japan 1997
Maruzen
Japan Science and Technology Agency
Subjects
Chemistry
chiral recognition
cyclopeptide
Exact sciences and technology
formation constant
hydrogen bond
NMR
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
α-Aminoacid
Octapeptide
Aminoester
Phenylalanine
Hydrochlorides
Cyclic peptides
Enantiomer
Proline
NMR spectrometry
Carbon 13
Recognition
Hydrogen bond
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Summary:The formation constant of the 1 : 1 complex of cyclo(L-Phe-L-Pro)4 (1) with L-PheOMe·HCl was about 13.2 times that of the complex with D-PheOMe·HCl. The 1 : 1 complex of 1 with L-PheOMe·HCl formed three intermolecular hydrogen bonds between Pro2 CO, Phe1 CO and the amino group, and Phe2 NH and the carbonyl group, whereas that with D-PheOMe·HCl formed only one between Phe1 CO and the amino group.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.45.1202