O

B = adenine, cytosine, guanine, thymine

NH(CH2)4NH-BOC

(CH2)4NH-Boc I

Scheme 4.2.2. (a) (i) HBTU, HOBt, DIPEA, DMF; (ii) Ac20, Pyr (1:10); (b) (i) TFA; (ii) DIPEA:DMF (1:9); (c) iterative cycles of: (i) piperidine/DMF (1:4); (ii) Fmoc-BBhoc-OH, HATU, iPr2NEt, Pyr, DMF; (iii) Ac20, Pyr, DMF; (d) (i) piperidine/DMF (1:4); (ii) Ac20, Pyr, DMF; (e) TFA:ethanedithiol:H20 (95:2.5:2.5); (f) lOequiv. DABCYL-SE, DMF:Pyr:NMM

(7:1:1); (g) piperidine/DMF (1:4); (h) lOequiv. DTT, DMF:H20:NMM (9:3:1); (i) 10 eq IAEDANS, DMF:H20:NMM (9:3:1); (j) [Pd(PPh3)4], morpholine, DMSO, DMF, 10% (based on 12). (DTT = dithiothreitol, HBTU =

0-(benzotriazol-l-yl)-N,N,N',N'-tetramethyl-uronium hexafluorophosphate, HOBt =

1-hydroxybenzotriazol)

322 | 4.2 Homogeneous DNA Detection 4.2.4

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