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Volumn 44, Issue 16, 2003, Pages 3381-3384

4-Amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylic acid (β-TOAC), the first spin-labelled, cyclic, chiral β-amino acid resolved in an enantiomerically pure state

Author keywords

Chiral nitroxides; Modified amino acids; Spin labelled amino acids

Indexed keywords

3 CARBOXYMETHYL 1 OXYL 2,2,6,6 TETRAMETHYL 4 PIPERIDONE; 4 AMINO 1 OXYL 2,2,6,6 TETRAMETHYLPIPERIDINE 3 CARBOXYLIC ACID; BETA AMINO ACID; CARBOXYLIC ACID DERIVATIVE; PIPERIDONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037436914     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00572-0     Document Type: Article
Times cited : (23)

References (50)
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    • 25 are as follows: (R)-3: -441 (c 0.25;MeOH). (S)-3: +456 (c 0.26; MeOH). (1′R,3S,4S)-4: +48 (c 0.25; MeOH). (1′R,3R,4R)-4: +41 (c 0.25; MeOH). (1′S,3R,4R)-4: -52 (c 0.26; MeOH). (1′S,3S,4S)-4: -47 (c 0.25; MeOH). (3S,4S)-5: +23 (c 0.1; MeOH). (3R,4R)-5: -22 (c 0.1; MeOH). (3S,4S)-6: -25 (c 0.1; MeOH). (3R,4R)-6: +23 (c 0.2; MeOH)
    • 25 are as follows: (R)-3: -441 (c 0.25;MeOH). (S)-3: +456 (c 0.26; MeOH). (1′R,3S,4S)-4: +48 (c 0.25; MeOH). (1′R,3R,4R)-4: +41 (c 0.25; MeOH). (1′S,3R,4R)-4: -52 (c 0.26; MeOH). (1′S,3S,4S)-4: -47 (c 0.25; MeOH). (3S,4S)-5: +23 (c 0.1; MeOH). (3R,4R)-5: -22 (c 0.1; MeOH). (3S,4S)-6: -25 (c 0.1; MeOH). (3R,4R)-6: +23 (c 0.2; MeOH).
  • 42
    • 85031200013 scopus 로고    scopus 로고
    • 13C NMR spectra of the nitroxide products in this study could only be obtained by preliminary use of the sodium dithionite reduction procedure proposed in Ref. 18
    • 13C NMR spectra of the nitroxide products in this study could only be obtained by preliminary use of the sodium dithionite reduction procedure proposed in Ref. 18.
  • 45
    • 85031196884 scopus 로고    scopus 로고
    • or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: (internat.) +44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk].
    • X-Ray quality crystals of (1′S,3R,4R)-4 were obtained by recrystallisation from acetonitrile solution. CCDC 204395 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at http://www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: (internat.) +44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk].
  • 50
    • 85031195032 scopus 로고    scopus 로고
    • 6 (aq.): MeCN 70:30, flow rate 0.5 mL/min, detection 254 nm, column temperature 30°C
    • 6 (aq.): MeCN 70:30, flow rate 0.5 mL/min, detection 254 nm, column temperature 30°C.


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