Synthesis and Application of 3′-Amino-Dye-Terminators For Dna Sequencing

Wojczewski, C.; Faulstich, Konrad; Engels, Joachim W.

doi:10.1080/07328319708002945

Cited by 9 publications

(3 citation statements)

References 9 publications

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“…1 H-NMR ( D 2 O ): 6.14 (t, HÀC(1')); 3.99 ± 4.28 (m, HÀC(4'), 2 HÀC(5')); 2.42 ± 2.61 (m, H a ÀC(2')); 2.18 ± 2.32 (m, H b ÀC(2')); 2.85 (t, NHCH 2 ); 1.25 ± 1.57 (m, 4 CH 2 ); 7.55 (s, HÀC (6)). 31 ); 4.24 (m, HÀC(4')); 4.11 ± 4.17 (m, H a ÀC(5')); 3.94 ± 4.02 (m, H b ÀC(5')); 3.18 (t, BocNHCH 2 ); 2.90 (t, CH 2 NÀC(4)); 2.23 ± 2.35 (m, H a ÀC(2')); 1.74 ± 2.00 (m, H b ÀC(2'), HÀC(3')); 1.13 ± 1.46 (m, 2 CH 2 , Me 3 C ); 7.70 (d, J(5,6) 7.54, HÀC(6)); 5.86 (d, HÀC (5)). 31 P-NMR ( D 2 O ): À 4.14 (d, P(g); À 9.74 (d, P(a)); À 19.44 (t, P(b)).…”

Section: Experimental Partmentioning

confidence: 99%

“…31 ); 4.24 (m, HÀC(4')); 4.11 ± 4.17 (m, H a ÀC(5')); 3.94 ± 4.02 (m, H b ÀC(5')); 3.18 (t, BocNHCH 2 ); 2.90 (t, CH 2 NÀC(4)); 2.23 ± 2.35 (m, H a ÀC(2')); 1.74 ± 2.00 (m, H b ÀC(2'), HÀC(3')); 1.13 ± 1.46 (m, 2 CH 2 , Me 3 C ); 7.70 (d, J(5,6) 7.54, HÀC(6)); 5.86 (d, HÀC (5)). 31 P-NMR ( D 2 O ): À 4.14 (d, P(g); À 9.74 (d, P(a)); À 19.44 (t, P(b)). (6)); 6.34 (d, 0.4 H, HÀC(5)); 6.14 (d, 0.6 H, HÀC(5)); 5.96 (m, HÀC(1')); 4.33 (m, HÀC(4')); 4.20 ± 4.26 (m, H a ÀC(5')); 3.99 ± 4.05 (m, HÀC(5')); 3.31 ± 3.37 (2t, CH 2 NÀC(4)); 2.87 ± 2.89 (dd, CH 2 NH 2 ); 2.34 ± 2.41 (m, H a ÀC(2')); 2.08 ± 2.14 (m, H a ÀC(2')); 1.97 ± 2.02 (m, H a ÀC(3')); 1.88 ± 1.95 (m, H a ÀC(3')); 1.54 ± 1.62 (m, 2 CH 2 ); 1.30 ± 1.32 (m, 2 CH 2 ).…”

Section: Experimental Partmentioning

confidence: 99%

“…There is a strong dependence of the spacer length between dye and nucleotide upon quantum yields and absorption coefficients [30] [31]. We, therefore, decided to elongate the spacer arm of the N 4 -modified cytidine derivative 14 with a rigid 4-(aminomethyl)cyclohexylcarbonyl moiety ( 3 18 and 19; Scheme 4).…”

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Synthesis of 3′-Sugar- and Base-Modified Nucleotides and Their Application as Potent Chain Terminators in DNA Sequencing

Stolze¹,

Koert²,

Klingel³

et al. 1999

HCA

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Two 3′‐modified and three base‐modified ddNTPs were synthesized and tested with several DNA polymerases for incorporation activity. Starting from 3′‐azido‐3′‐deoxythymidine (AZT; 1), we were able to produce 3′‐deoxy‐3′‐isocyanato‐thymidine and 3′‐deoxy‐3′‐isothiocyanatothymidine (3 and 4, resp.) in a rapid synthesis based on the solid‐support approach (Scheme 1). These 3′‐functionalities could be used to attach a spacer molecule via urea and thiourea groups, respectively. Since the thus‐obtained tethered nucleotides 7 and 8 can be used to label with fluorescent dyes (cf. Scheme 5), they are convenient building blocks for practical applications in DNA sequencing. Furthermore, we synthesized, via 14 (Scheme 2), 17 (Scheme 3), and 19 (Scheme 4), the N4‐modified dideoxycytidine 5′‐triphosphate dye derivatives 22, 23, and 24, respectively, with different lengths of linkers between the base residue and the dye (Scheme 5). Base‐specific termination for the derivatives 22 and 24 was demonstrated (Fig. 2a and 2b).

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Section: Experimental Partmentioning

confidence: 99%

Section: Experimental Partmentioning

confidence: 99%