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13 C and 15 N NMR chemical shift assignments of N ‐1‐(2‐ azidoethyl)‐4‐ R ‐pyrimidin‐2‐ones by 1 H,X HMQ(B)C with z ‐gradient selection
Author(s) -
Kolehmainen Erkki,
Lappalainen Kari,
Šaman David,
Holý Antonin,
Günter Jaroslav
Publication year - 1998
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/(sici)1097-458x(199806)36:6<442::aid-omr314>3.0.co;2-g
Subject(s) - chemistry , chemical shift , substituent , carbon 13 nmr , stereochemistry , ring (chemistry) , proton , molecule , derivative (finance) , cytosine , group (periodic table) , crystallography , organic chemistry , dna , physics , quantum mechanics , financial economics , economics , biochemistry
13 C and 15 N NMR chemical shift assignments based on z ‐gradient selected 1 H,X (X= 13 C and 15 N) HMQC and HMBC experiments are reported for N ‐1‐(2‐azidoethyl)pyrimidin‐2‐one (ring system of cytosine), its five 4‐R derivatives [where R=NH 2 , OCH 3 , N(CH 2 ) 4 , NHCH 2 CH(CH 3 ) 2 and N(CH 3 ) 2 ] and 2‐azidoethyl tosylate. The possibilities of detecting all nitrogens in these molecules containing (i) an azido group at N‐1 and (ii) an electronegative substituent at C‐4 are limited. First, the terminal nitrogen of the azido group is difficult to observe because the nearest proton (in a CH 2 group) is located four bonds away from it. Second, in contrast to N‐1, N‐3 in N ‐1‐(2‐azido‐ethyl)‐4‐pyrimidin‐2‐ones remained undetected. For that reason, an unsubstituted derivative (R=H) was also prepared, where N‐3 was easily observed. © 1998 John Wiley & Sons, Ltd.