15N NMR spectroscopy. 19—spectroscopic characterization of cyclodipeptides (2,5‐dioxopiperazines)
作者:
Hans R. Kricheldorf,
期刊:
Organic Magnetic Resonance
(WILEY Available online 1980)
卷期:
Volume 13,
issue 1
页码: 52-58
ISSN:0030-4921
年代: 1980
DOI:10.1002/mrc.1270130111
出版商: John Wiley&Sons Limited
数据来源: WILEY
摘要:
AbstractVarious cyclodipeptides containing glycine, alanine, leucine, valine, phenylalanine, phenylglycine and sarcosine units were synthesized by cyclization of dipeptide pentachlorophenyl esters. The13C and natural abundance15N NMR spectra of these heterocycles were measured in trifluoroacetic acid and compared with the spectra of the corresponding amino acids and polypeptides. The13C NMR carbonyl signals of all cyclodipeptides show a 1.5–4.0 ppm upfield shift relative to the corresponding polypeptides. The15N NMR signals show no such consistent relationship. The substituent effects and the neighbouring residue effects observed in the15N NMR spectra of the cyclodipeptides are different from those of polypeptides, while the one bond NH coupling constant ofcisandtransamide groups was almost identical. The nitrogen and the carbonyl signal of the Gly units in cyclo‐Gly‐Phe show an extraordinary downfield shift, reflecting the interaction of the phenyl group with the 2,5‐dioxopipera
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