Determination of n J(CH) coupling constants. W. Bermel ENC workshop
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1 W. Bermel ENC workshop.. 016
2 C. Thiele
3 Hymenistatin (+)-Isopinocampheol ( (+)-IPC ) Pro(1) Pro() O H C H Ile(8) C H C H O C H C H C H C C H C H N C H O C C H N C H H C C H C O N H H C H C C H C C C H C H C H Tyr() O H H N C O C H H C C H Ile(7) O C H C C H N H O C Leu(6) C H C H C H C H N H C O C H H C C H N H C C C H C H N H O Pro(5) H C C H C H Val() 0mM in DMSO 585mM in CDCl R.K. Konat, D.F. Mierke, H.Kessler, B. Kutscher, M. Bernd & R. Voegeli, Helv. Chim. Acta 76, 169 (199)
4 HSQC OH s 7s 5 a 8 7a
5 Splitting in F Hetloc Hecade a/b HSQC-TOCSY HSQMBC HMBC-JRes Splitting in F1 J-HMBC Exside SJS-HSQC 5
6 Hetloc: x-filtered H,H TOCSY (F1 coupled) H H H 1 C X X t m 80ms n J(CH) 1 J(CH) * cnst H/C10 expt 7min H10/C sign relative to 1 J(CH) (positive) 6
7 Hetloc: x-filtered H,H TOCSY (F1 coupled) IPC cnst Ha H H/H
8 Hetloc: x-filtered H,H TOCSY (F1 coupled) OH J(H,C) J(H,C) J(H,C10) Hz Hz + 6. Hz (Ha) (Hs) 8 6 J(H,C1)* Hz 9 5 J(H,C7)* - 0. Hz (H7a) J(H,C7)* Hz (H7s) H/H5 overlap J(H1,H).0 Hz * t m >= 80ms digital resolution 0.16 Hz/pt 8
9 Hecade: H,C HSQC-TOCSY (F1 coupled) H H H 1 C X X t m 80ms n J(CH) 1 J(CH) * cnst H/C10 expt 6min H10/C sign relative to 1 J(CH) (positive) 9
10 Hecade: H,C HSQC-TOCSY (F1 coupled) OH J(H,C) J(H,C) J(H,C5) -.19 Hz -1.6 Hz Hz 8 6 J(H,C10) + 6. Hz 9 5 J(H,C7)* - 0.8Hz J(H,C1)** Hz C1/C partial overlap J(H1,H).0 Hz * t m >= 80ms ** t m >= 80ms + td1 k (NUS) digital resolution 0.16 Hz/pt 10
11 Hetloc: x-filtered H,H TOCSY (F1 coupled) Hecade: H,C HSQC-TOCSY (F1 coupled) IPC H/C10 k 0.6 k 0.1 8k 0.16 td_eff resolution [Hz/pt] (LP + zf) k 0.6 k 0.1 8k 0.16 Hymenistatin Ile[8] Ha/Cg 1k. k 1.61 k k k 0.0 td_eff resolution [Hz/pt] (LP + zf) 1k. k 1.61 k k k
12 Hecade: H,C HSQC-TOCSY (F1 coupled) IPC t m 80ms td1 56 NUS 50%/51 5%/1k 1.5%/k C C
13 Hecade: H,C HSQC-TOCSY (F1 coupled) IPC t m 0ms 5ms 60ms 80ms 100ms C C7 5 C 0 C5 5 C/C
14 a/b H,C HSQC-TOCSY ( 1 J-IPAP) H H H 1 C X X n J(CH) 1.5 t m 5ms H/C expt 6min sign relative to 1 J(CH) (positive) 1
15 a/b H,C HSQC-TOCSY ( 1 J-IPAP) OH J(H,C) J(H,C) J(H,C5) -. Hz Hz Hz 8 6 J(H,C7) Hz 5 J(H,C10) Hz 9 C1/C partial overlap t m = 5ms J(H1,H).0 Hz digital resolution 0.16 Hz/pt 15
16 J-HMBC: HMBC + J evolution H H H 1 C X X H/C n J(CH) * SCALEF 1.0 no sign information expt 1hmin SCALEF always maximum according to td1 and cnst1 16
17 J-HMBC: HMBC + J evolution OH J(H,C) J(H,C5) J(H,C10) 1.6 Hz 1.57 Hz 6.5 Hz 8 6 J(H,C7)* < 0.6Hz J(H,C9)* < 0.70 Hz C1/C partial overlap * cnst 1 = 0.5 Hz td1 = 56 digital resolution 0.5 Hz/pt 17
18 J-HMBC: HMBC + J evolution resolution * swh1 td1 * k 1 SCALEF 1 swh1 = inf1 SCALEF = * d6 td1 * inf1 td1 * inf1 * k td1 * inf1 * d6 d6 = 1 cnst1 * 1 k * d6 = * cnst1 k lp, zf: k = cnst1 18
19 J-HMBC: HMBC + J evolution H/C10 si k k k 8k 16k LP only cnst1 = 8Hz td1 = 56 SCALEF = 6 resolution (LP + zf) = Hz 19
20 J-HMBC: HMBC + J evolution H/C10 td k SCALEF cnst1 = 8Hz resolution (LP + zf) = Hz 0
21 J-HMBC: HMBC + J evolution H/C10 cnst1 8 Hz Hz Hz 1 Hz 0.5 Hz SCALEF td1 = 56 1
22 J-HMBC: HMBC + J evolution cnst1 SCALEF resol. J(H,C) J(H,C) J(H,C5) J(H,C7) 5 J(H,C9) J(H,C10) 8 Hz 6 Hz/pt 8.56 Hz 8.7 Hz 8.67 Hz ** 8.96 Hz 8.76 Hz Hz 1 Hz/pt. Hz.19 Hz.6 Hz **.0 Hz 5.75 Hz Hz 1 Hz/pt.17 Hz.1 Hz.18 Hz **.16 Hz 6.5 Hz 1 Hz Hz/pt * 1.18 Hz 1.9 Hz 1.5 Hz 1.09 Hz 6.5 Hz 0.5 Hz Hz/pt * 1.6 Hz 1.57 Hz 0.6 Hz 0.70 Hz 6.5 Hz 1.55 Hz Hz + Hecade 0.16 Hz/pt -.19 Hz -1.6 Hz Hz Hz n.a Hz td1 = 56 + td1 = 1K * C1/C overlap ** signal too weak
23 J-HMBC: HMBC + J evolution H td(scalef) 18(1) 56(6) 51() 1k() C10 C C C5 0 5 C cnst1 = 8Hz resolution (LP + zf) = Hz
24 J-HMBC: HMBC + J evolution cnst1 (SCALEF) 8Hz(6) Hz(1) Hz() 1Hz(8) H 0.5Hz(98) C10 C C C5 0 5 C td1 = 56
25 HSQMBC: long range HSQC H H H 1 C X X 0.5 no sign information expt 9min H/C
26 HSQMBC: long range HSQC 10 J(H,C) J(H,C) 1.96 Hz 1.61 Hz OH J(H,C5) 1.6 Hz J(H,C6)* 1.1 Hz J(H,C7)* 0.80 Hz 5 J(H,C9)* 1.08 Hz 9 J(H,C10) 6. Hz * from antiphase C1/C partial overlap selective, cnst1 = Hz digital resolution 0.16 Hz/pt 6
27 HSQMBC: long range HSQC transfer amplitude sin ( p k J CH D ) * P cos( p n J HH D ) k = 1, n BIRD r,x removes 1 J peaks CPMG (XY16) selective remove J HH contributions IPAP two separate spectra 7
28 HSQMBC: long range HSQC 1D BIRD CPMG selective HC10 HC digital resolution 0.16 Hz/pt cnst1 = Hz 8
29 HSQMBC: long range HSQC - IPAP H H H 1 C X X no sign information n J(CH) H/C expt 9min
30 HSQMBC: long range HSQC 1D BIRD - IPAP selective - IPAP HC10 HC digital resolution 0.16 Hz/pt cnst1 = Hz 0
31 HSQMBC: long range HSQC - IPAP 10 J(H,C) BIRD.9 Hz selective.16 Hz OH J(H,C) 1.71 Hz 1.71 Hz J(H,C5) 1.78 Hz 1.8 Hz J(H,C6) Hz* 1.5 Hz* J(H,C7) Hz* 1.1 Hz* 9 5 J(H,C9) 1. Hz 1.Hz J(H,C10) 6. Hz 6.9 Hz C1/C partial overlap * poor signal-to-noise cnst1 = Hz digital resolution 0.16 Hz/pt 1
32 HSQMBC: long range HSQC - COSY/TOCSY IPAP TOCSY COSY H H H 1 C X X H H H 1 C X X H X H X H H H 1 C X X H X
33 HSQMBC: long range HSQC - COSY/TOCSY IPAP H H H 1 C X X H X t m 5ms n J(CH) H/C10 H10/C expt 6h5min
34 HSQMBC: long range HSQC - IPAP COSY [Hz] TOCSY [Hz] H7s, H/5 H7s, H10 J(H,C1) OH J(H,C) J(H,C) J(H,C5) H, H/5, H1 H, Ha H, H7s H, H7s, H10 H, H7s H, H7s 8 6 J(H,C6) J(H,C7) H1 5 J(H,C9) C1/C partial overlap J(H,C10) +6. H/5 +6. H,H1 digital resolution 0.16 Hz/pt
35 HSQMBC: long range HSQC - selective IPC H Hymenistatin Ha region
36 EXSIDE: selective long range HSQC + J-evolution H H H 1 C X X H/C n J(CH) * SCALEF 1.0 no sign information expt 1h7min
37 EXSIDE: selective long range HSQC + J-evolution J(H,C1) 0.51 Hz 10 J(H,C).0 Hz OH J(H,C) J(H,C5) J(H,C6) J(H,C7) 1.51 Hz 1.61 Hz < 0.8 Hz* < 0.8 Hz* 9 5 J(H,C9) 0.5 Hz J(H,C10) 6. Hz C1/C partial overlap * smaller than n 1/ cnst16 = 80, td1 = 51, cnst1 = digital resolution 0.15 Hz/pt 7
38 EXSIDE: selective long range HSQC + J-evolution C5 C C H C10 C7 cnst16 resol Hz/pt C8 cnst16 resol Hz/pt C1 C C9 cnst16 resol Hz/pt td1 = 56 8
39 EXSIDE: selective long range HSQC + J-evolution C C5 C C9 C10 H C6 cnst16 resol Hz/pt cnst16 resol Hz/pt C1 C7 C8 cnst16 resol Hz/pt td1 = 51 9
40 EXSIDE: selective long range HSQC + J-evolution H C1 cnst16 td cnst16 td C C5 C C9 C10 C6 C C8 cnst16 td1 50 1k resol. 0.1 Hz/pt 0
41 EXSIDE: selective long range HSQC + J-evolution H cnst16 td1 5 5%/k C1 cnst16 td %/1k C C5 C C9 C10 C6 C C8 cnst16 td1 50 1k resol. 0.1 Hz/pt 1
42 SJS-HSQC: HSQC + J-evolution and E.COSY H H H 1 C X X J(HC10) * cnst J(HC) * cnst H10/C10. J(HHs) Hs/C cnst16 = 0, td1 = 51 J(HHs) and J(HC) have opposite sign
43 SJS-HSQC: HSQC + J-evolution and E.COSY 10 J(H,C1) J(H,C) 0.8 Hz -.16 Hz OH J(H,C) J(H,C5) -1.6Hz J(H,C) -1.6Hz 1.71 Hz J(H,C7) < 0. Hz* (Ha) (Hs) 9 5 J(H,C9) 0.87 Hz J(H,C10) 6.9 Hz * from line broadening cnst16 = 10, td1 = 51 expt 1h19min decoupling during acquisition digital resolution 0.10 Hz/pt
44 HMBC-JRes: HMBC + J-resolved H H H 1 C X X sequence I sequence II H/C10 H/C expt 5min n J(CH) no sign information magnitude
45 HMBC-JRes: HMBC + J-resolved OH J(H,C) J(H,C) J(H,C5) 5 J(H,C9).1 Hz 1.69 Hz 1.70 Hz 1.0 Hz 9 J(H,C10) 6.1 Hz C1/C partial overlap C/C6 partial overlap signal too weak cnst16 = 5, cnst1 = Hz digital resolution 0.16 Hz/pt 5
46 HMBC-JRes: HMBC + J-resolved sequence II H/C10 cnst magnitude 6
47 Hz J(H,C1) J(H,C) J(H,C) J(H,C5) J(H,C6) J(H,C7) 5 J(H,C9) J(H,C10) Hetloc Hecade J-HMBC < 0.6 < a/b HSQC- TOCSY HSQMBC sel. HSQMBCsel. IPAP HSQMBC- TOCSY EXSIDE < 0.8 < HMBC-JRes SJS-HSQC <
48 NS td1 expt S/N cnst16 cnst1 Hetloc min 95 1 Hecade 56 6min 67 1 a/b HSQC- TOCSY J-HMBC min 1hmin HSQMBC sel. HSQMBCsel. IPAP HSQMBC-TOCSY EXSIDE min* 9min* 6h5min* -COSY 66 1h7min* H H HMBC-JRes 56 5min 15 5 SJS-HSQC 51 1h19min* * selective pulse signal:.1-.0, noise: at C10 (CH ) 8
49 Thank You 9
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