Table 1.

Comparison of ¹H and ¹³C NMR Data of Naturally Occurring Scytonemide A with Synthesized Scytonemide A in DMSO-d₆ ^a

	Natural scytonemide Ab			Synthetic 1
	position	δC, type	δH, mult., (J in Hz)	δC, type	δH, mult., (J in Hz)
Tyr1	1	172.93, C		172.39, C
	2	74.0, CH	3.53, dd (11.3, 2.8)	73.5, CH	3.54, dd (11.2, 2.4)
	3a	40.1, CH2	3.04, dd (13.5, 2.4)	39.45, CH2	3.05, dd (13.4, 2.4)
	3b		2.48, ddd (13.5, 13.5, 2.4)		2.48, dd (13.4, 11.2)
	4	127.6, C		127.32, C
	5/9	131.4, CH	6.86, d (8.5)	130.91, CH	6.86, d (8.5)
	6/8	115.3, CH	6.61, d (8.5)	114.78, CH	6.61, d (8.5)
	7	156.4, C		155.8, C
	OH				9.15, s
Gly2	1	171.28, C		170.84, C
	2a	40.6, CH2	4.32, m	39.88, CH2	4.32, dd (16.8,10.3)
	2b		3.42, m		3.42, dd (16.8, 2.8)
	NH		7.78, dd (10.0, 2.6)		7.75, dd (10.3, 2.8)
D-Gln3	1	172.58, C		172.14, C
	2	53.8, CH	4.33	53.52, CH	4.31, dt (6.8, 6.5)
	3a	25.7, CH2	1.85, m	25.23, CH2	1.85, m
	3b		1.76, m		1.76, m
	4a	31.8, CH2	2.11	31.26, CH2	2.11, ddd (15.5, 10.3, 5.6)
	4b		1.99		1.99, ddd (15.5, 10.3, 5.6)
	5	173.68, C		173.20, C
	NH		8.55, d (6.3)		8.54, d (6.5)
	NH2		7.33, br s		7.31, br s
			6.78, br s		6.77, br s
Ile4	1	170.15, C		169.75, C
	2	58.0, CH	4.17, dd (9.2, 3.9)	57.51, CH	4.18, dd (9.1, 3.9)
	3	35.7, CH	2.06, m	35.22, CH	2.06, m
	3-Me	16.4, CH3	0.86, d (7.0)	15.95, CH3	0.86, d (7.0)
	4	24.1, CH2	1.28, m	23.61, CH2	1.28, m
	5	12.5, CH3	0.83, m	11.96, CH3	0.84, t (7.4)
	NH		8.17, d (9.3)		8.17, d (9.1)
Ser5	1	172.56, C		172.06, C
	2	53.0, CH	4.93, m	52.58, CH	4.90, td (9.5, 6.5)
	3a	62.8, CH2	3.87, dd (10.0, 10.0)	62.22, CH2	3.89, ddd (9.9, 9.5, 5.8)
	3b		3.60, dd (9.8, 6.0)		3.62, ddd (9.9, 6.5, 5.8)
	OH				5.55, t (5.8)
	NH		7.36, d (9.0)		7.37, d (9.5)
Val6	1	170.31, C		169.77, C
	2	59.7, CH	4.01, dd (7.7, 4.2)	59.18, CH	4.01, dd (7.6, 4.2)
	3	29.0, CH	2.22, m	28.44, CH	2.24, sept d (7.0, 4.2)
	3-Me	17.4, CH3	0.90 d (7.0)	16.97, CH3	0.89, d (7.0)
	4	19.7, CH3	0.93, d (7.0)	19.18, CH3	0.93, d (7.0)
	NH		8.40, br s		8.16, d (7.6)
Leu7	1	166.0, CH	6.80, d (1.8)	165.60, CH	6.81, d (1.8)
	2	49.6, CH	4.37, m	49.11, CH	4.37, dddd (10.6, 9.3, 4.7, 1.8)
	3a	40.6, CH2	1.05	39.80, CH2	1.05, ddd, (13.6, 10.6, 5.3)
	3b		0.81		0.81, m
	4	24.8, CH	1.29, m	24.26, CH	1.29, m
	4-Me	23.4, CH3	0.80, d (6.7)	22.82, CH3	0.80, d (6.7)
	5	21.7, CH3	0.72, d (6.5)	21.16, CH3	0.72, d (6.5)
	NH		7.90, d (9.4)		7.78, d (9.3)

^aFrequency: Natural 900 MHz for ¹H, 226 MHz for ¹³C, synthetic 700 MHz for ¹H, 176 MHz for ¹³C.

^bJ. Nat. Prod. 2010, 73, 1927–1932.