Catalysis of nucleobase via multiple hydrogen-bonding interactions: Acceleration of aminolysis of 6-chloropurine derivatives by uracils [5]

Journal of the American Chemical Society

Volumn 121, Issue 33, 1999, Pages 7704-7705

  Tominaga, Masahide ^a   Konishi, Katsuaki ^a   Aida, Takuzo ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 6 CHLOROPURINE; NUCLEIC ACID BASE; PURINE DERIVATIVE; UNCLASSIFIED DRUG; URACIL;

CATALYSIS; CHEMICAL REACTION; COMPLEX FORMATION; HYDROGEN BOND; LETTER; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0033603854     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990944s     Document Type: Letter

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33. 1H NMR by comparison with the authentic sample.
34. 2 of 1 (δ 4.24 → 4.33) and 5-H (δ 5.51 → 5.52), 1′-H (δ 5.83 → 5.84), and NH ( δ 8.03 → 8.21) of 8, indicating a base-paring interaction between 1 and 8.
35. -1. These values are comparable to those reported for similar double hydrogen-bonded complexes such as the adenine-thymine base pair (see ref Sf).
36. See Supporting Information.
37. uncat).
38. uncat values at 20, 30, and 40°C.
39. Although four different hydrogen-bonding modes are possible for the ternary complexation, syn-10 and anti-10 are the most plausible, since the other two modes appear to suffer from a steric hindrance of the N(9) substituent (see Supporting Information).
40. 6, 30°C) at δ 155.0 (C(2)) and 168.6 (C(4)) are both downfield from those of 5 [δ 150.1 (C(2)) and 163.4 (C(4))], indicating lower electron densities at the C=O moieties in 7.