Table 1 1H NMR (600 MHz) and 13C NMR (125 MHz) data for [4-R–Phe]-sansanmycin H (1–4)

From: Precursor-directed biosynthesis of new sansanmycin analogs bearing para-substituted-phenylalanines with high yields

  

Comp. 1

Comp. 2

Comp. 3

Comp. 4

Position a

Multi

δC( )b

δH( )b

δC( )b

δH( )b

δC( )b

δH( )b

δC( )b

δH( )b

Uracil-2

N–CO–N

147.8(147.0)

 

150.6

 

150.5

 

150.8

 

Uracil-4

CO–N

160.9

 

163.4

 

163.1

 

163.8

 

Uracil-5

CH

105.7(105.5)

5.83(5.55)

102.1(102.2)

5.63(5.45)

102.1

5.64(5.46)

102.0(102.2)

5.61(5.45)

Uracil-6

CH

141.9(141.6)

7.25(6.89)

139.9

7.44(7.11)

140.0(139)

7.45(7.11)

139.8(139.2)

7.43(7.11)

Sugar-1

O–CH–N

96.0(96.6)

6.09(6.11)

92.3(91.8)

5.96(6.00)

92.3(91.7)

5.96(5.99)

92.4(91.9)

5.96(5.99)

Sugar-2

O–CH

75.9(75.4)

4.49(4.15)

71.7(71.6)

4.38(4.26)

71.7(71.6)

4.38(4.280

71.8(71.6)

4.37(4.28)

Sugar-3

CH2

32.2

2.46

33.9

2.84

2.51

33.9

2.86

2.49

33.9

2.82

2.49

Sugar-4

>C=

141.2

 

141.1

 

141.1

 

141.1(166.5)

 

Sugar-5

–CH=

98.9(99.3)

5.93(5.96)

96.7

 

96.7

5.84(5.82)

96.8

5.83

DABA-1

CO–N

170.3(170.0)

 

166.8(166.5)

5.83(5.81)

166.9(166.5)

 

166.9

 

DABA-2

CH

58.9

4.49

54.7

4.66

54.7

4.66

54.8

4.65

DABA-3

CH

56.2

4.15

50.1

4.85

50.1

4.85

50.7(50.1)

4.14

DABA-4

CH3

16.1(16.6)

1.19(0.59)

13.8(14.8)

1.07(0.64)

13.8(14.8)

1.07(0.65)

13.8(14.9)

1.07(0.61)

DABA–N–CH3

N–CH3

33.1

2.93

30.1

2.91

27.0(29.7)

2.55(2.91)

30.0

2.91

Ureido

N–CO–N

160.9

 

157.3

 

157.3(157.1)

 

157.3

 

4-R–Phe-1

–COOH

180.1

 

173.6

 

173.6

 

175.6

 

4-R–Phe-2

CH

54.7(54.4)

4.26(4.22)

55.6(53.2)

3.90(4.00)

55.8

3.91

54.7

3.90(4.14)

4-R–Phe-3

CH2

40.8(44.0)

2.85(2.67) 3.07

37.7

2.99

2.89

37.5

2.97

2.88

37.3

2.72

2.94

4-R–Phe-1′

ArC

137.7(137.6)

 

139.3(138.9)

 

139.5

 

139.8(140.4)

 

4-R–Phe-2′

ArCH

132.1

7.12

127.2(127.5)

7.24(7.19)

130.4(130.1)

7.38(7.32)

130.0

7.11

4-R–Phe-3′

ArCH

131.9

7.17

131.1(131.4)

7.21(7.14)

131.5(131.9)

7.15(7.08)

128.5

6.78

4-R–Phe-4′

ArC

139.3

 

138.7

 

118.6

 

138.8

 

4-R–Phe-5′

ArCH

131.9

7.17

131.1(131.4)

7.21(7.14)

131.5(130.9)

7.15(7.08)

128.5

6.78

4-R–Phe-6′

ArCH

132.1

7.12

127.2(127.5)

7.24(7.19)

130.4(130.1)

7.38(7.32)

130.0

7.11

4-Me–Phe–Me/4–MeO–Phe–OMe

–CH3

23.0

2.29

    

54. 8

3.71

m-Tyr-1

CO–N

179.4

 

175.5

 

175.5

 

174.8

 

m-Tyr-2

CH

54.4(40.8)

3.97(4.26)

52.1

3.66(4.13)

52.3

3.67

52.4(50.8)

3.68

m-Tyr-3

CH2

42.9(44.0)

2.46(2.66)

40.9

2.20(2.56) 2.71

40.9(42.0)

2.71(2.55)

40.9(42.1)

2.20(2.57)

2.71(2.50)

   

2.85

   

2.20

  

m-Tyr-1′

ArC

141.4

 

138.6

 

139.0

 

140.5

 

m-Tyr-2′

CH

118.1(117.9)

6.67(6.71)

116.1(116.0)

6.40(6.68)

119.6(116.1)

6.40(6.68)

116.2(116.1)

6.69

m-Tyr-3′

Ar–C–O

161.3(161.2)

 

158.3(157.3)

 

158.1

 

157.3(157.2)

 

m-Tyr-4′

ArCH

120.2

6.45

113.2(113.0)

6.47(6.65)

113.2(113.0)

6.48(6.63)

113.2(112.9)

6.63(6.72)

m-Tyr-5′

ArCH

133.0

7.15

128.5

6.94(7.05)

128.5(128.8)

6.94(7.04)

130.4

7.05

m-Tyr-6′

ArCH

121.9(120.1)

6.63(6.69)

119.6(119.0)

6.60(6.63)

119.7

6.64(6.62)

119.5

6.61

Met-1

CO–N

177.4

 

174.8

 

172.3(174.8)

 

174.4

 

Met-2

CH

55.8(55.9)

4.22

53.1

4.03

52.5

4.04(4.13)

53.2

4.02

Met-3

CH2

33.8(33.7)

1.85

31.8(31.1)

1.85

31.8(31.1)

1.86(1.85)

31.6

1.85

   

1.94

 

1.75

 

1.75

 

1.76

Met-4

CH2

30.7

2.68

30.0

2.41

30.0

2.43

30.0(29.7)

2.47(2.38)

Met–S–CH3

CH3

17.0

2.05

14.4(14.5)

1.99

14.5

1.99

14.5

1.99

  1. The spectra of compound 1 were recorded in D2O (pD=8) and the others in DMSO. The chemical shifts (δ) are given in p.p.m.
  2. aAbbreviations for the structure units are: m-Tyr, meta-tyrosine; 4-R–Phe=4-R-phenylalanine and R=Me for Comp. 1, Cl for Comp. 2, Br for Comp. 3 and MeO for Comp. 4, DABA, 2-amino-3-methyl-aminobutyric acid, Met, methionine.
  3. bThe data in the parentheses are the extra signals due to rotational conformers around the amide bonds, which is often observed in peptides especially those containing N-methylated amino acids or proline.
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