Govindaraju T, Gonnade Rajesh G, Bhadbhade Mohan M, Kumar Vaijayanti A, Ganesh Krishna N
Division of Organic Chemistry (Synthesis) and Centre for Materials Characterisation (X-ray Facility), National Chemical Laboratory, Pune 411008, India.
Org Lett. 2003 Aug 21;5(17):3013-6. doi: 10.1021/ol034933m.
[structure: see text] The synthesis of ethyl cis-(1S,2R/1R,2S)-2-aminocyclohex-1-yl-N-(thymin-1-yl-acetyl) glycinate (10a and 10b) via enzymatic resolution of the key racemic intermediate trans-2-azido cyclohexanols 3 is reported. The crystal structures of 10 show equatorial disposition of the tertiary amide group, with the torsion angle beta in the range 60-70 degrees. The PNA oligomers incorporating these show differential effects in hybridizing with complementary DNA and RNA.
[结构：见正文] 报道了通过关键外消旋中间体反式-2-叠氮基环己醇3的酶促拆分合成顺式-(1S,2R/1R,2S)-2-氨基环己-1-基-N-(胸腺嘧啶-1-基-乙酰基)甘氨酸乙酯(10a和10b)。10的晶体结构显示叔酰胺基团处于赤道位置，扭转角β在60 - 70度范围内。掺入这些的肽核酸寡聚物在与互补DNA和RNA杂交时表现出不同的效果。
