Table 1.

¹H and ¹³C NMR Analysis of Nonlabeled and Labeled Mithramycin SK (2)

position	1H δ (ppm)a multiplicity (JHz)	13C δ (ppm)a	1-13Cb		1,2-13C2b
			shift (ppm)	relative enrichments	Jcc (Hz)
1		203.5	197.5	3.0	45
2	4.70 d (11.5)	78.2	78.1		45
3	2.48 overlap	43.7	45.3	3.3	44
4a	3.15 dd (16, 3)	28.3	30.5		44
4e	2.99 overlap
4a		136.9	139.9	7.7	66
5	6.87 s	101.7	101.3		61
6		159.9	160.3	8.1	69
7		111.0	111.7		69
7-CH3	2.15 s	7.9	8.6
8		156.2	161.9	4.7	61
8a		108.0	108.8		61
9		165.3	177.2	2.7	69
9a		108.5	108.7		69
10	6.89 s	117.0	113.4		66
10a		139.1	140.8	6.2	61
1′	4.25 dd (3.4, 1.5)	78.3	80.7		43
1′-OCH3	3.55 s	60.0	60.5
2′	4.32 d (3.4)	79.5	80.6	6.4	43
3′		209.9	212.6	3.2	39
1A	5.37 dd (10, 2)	97.0
2Aa	1.86 ddd (12, 12, 10)	37.5
2Ae	2.48 overlap	37.5
3A	3.78 ddd (12, 9, 5)	81.3
4A	3.09 dd (9, 9)	75.4
5A	3.55 overlap	72.6
6A (CH3)	1.34 d (6)	18.0
1B	4.75 dd (10, 2)	99.9
2Ba	1.59 ddd (12, 12, 10)	40.0
2Be	2.20 ddd (12, 5, 2)	40.0
3B	3.58 overlap	71.4
4B	3.01 dd (9, 9)	77.6
5B	3.41 dq (9, 6)	72.6
6B (CH3)	1.34 d (6)	17.7
1C	5.14 dd (10, 2)	100.8
2Ca	1.62 ddd (12, 12, 10)	37.9
2Ce	2.51 ddd (12, 5, 2)	37.9
3C	3.68 overlap	81.8
4C	3.05 dd (9, 9)	75.7
5C	3.33 dq (9, 6)	72.6
6C (CH3)	1.34 d (6)	17.9
1D	4.70 dd (10, 2)	100.3
2Da	1.80 ddd (12, 12, 10)	32.5
2De	1.95 ddd (12, 5, 2)	32.5
3D	3.88 ddd (12, 5, 3)	77.3
4D	3.72 bs	68.9
5D	3.70 overlap	71.0
6D (CH3)	1.34 d (6)	16.5
1E	4.98 dd (9.5, 2)	97.9
2Ea	1.56 dd (13, 9.5)	44.3
2Ee	1.90 dd (13, 2)	44.3
3E		70.7
3E-CH3	1.22 s	27.0
4E	2.99 d (9)	76.8
5E	3.65 overlap	71.0
6E (CH3)	1.22 d (6)	26.3
4′	2.35 s	26.3	27.2		39

^a Data collected in acetone-d₆ at 500 MHz (1H NMR) and 125.7 MHz (¹³C NMR).

^bData collected in methanol-d₄ at 75.4 MHz.