AMIDES AS A NEW-TYPE OF BACKBONE MODIFICATION IN OLIGONUCLEOTIDES
AMIDES AS A NEW-TYPE OF BACKBONE MODIFICATION IN OLIGONUCLEOTIDES
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DOI：
10.1002/anie.199402261
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发表时间：
1994-02-01
期刊：
影响因子：
--
通讯作者：
FREIER, SM
中科院分区：
文献类型：
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作者：
DEMESMAEKER, A;WALDNER, A;FREIER, SM
羧酸6用0-（1H-苯并三唑-1-基）-N，N，N '，N'-四甲基脲四氟硼酸盐（TBTU）和N-羟基苯并三唑丙醇活化，然后与胺8a-c偶联。在酰胺二聚体9a（R= H）的情况下，通过1H NMR光谱法仅检测到方案2中描绘的旋转异构体。然而，在溶液中发现了N-二取代酰胺9 b、9 c的两种旋转异构体，并通过1HNMR NOE实验进行了鉴定。在这两种情况下，主要的旋转异构体是方案2中所示的旋转异构体（旋转异构体比率约为100%）。4：1在CDCI中，在室温下）。
Carboxylic acid 6 was activated with 0-(1 H-benzotriazol-1-y1)-N, N, N', N'-tetramethyluronium tetrafluoroborate (TBTU) and N-hydroxybenzotriazole ['ol and then coupled with amines 8a-c. Only the rotamer depicted in Scheme 2 was detected by'H NMR spectroscopy in the case of the amide dimer 9a (R= H). However, both rotamers of the N-disubstituted amides 9b, 9c were found in solution and identified by'HNMR NOE experiments.["] The major rotamer was, in both cases, the one shown in the Scheme 2 (rotamer ratio ca. 4: 1 in CDCI, at room temperature).