Proton Chemical Shift and J-coupling Values for Low Molecular Weight Metabolites.

 

The following table lists proton chemical shift and J-coupling values for metabolite considered to be present at sufficient concentrations, either in normal or diseased states, and observable by 1H MR spectroscopy of tissue. The table is reproduced from:

V. Govindaraju, K. Young, and A. A. Maudsley.  Proton NMR chemical shifts and coupling constants for brain metabolites, NMR in Biomedicine, 13:129-153 (2000).

This publication should be referenced in any articles making use of this information. As additional results not included in the published table are obtained, they will be included here.

All data were obtained at 37oC, for pH of 7.0 in H2O, or 6.6 in D2O. Chemical shifts are reported with reference to DSS-trimethyl singlet resonance at 0.0000 ppm, and multiplicity definitions are: s, singlet; d, doublet; t, triplet; q, quartet; qu, quintet; m, other multiplet. The multiplicity given here was observed in conventional 1D spectra recorded at 500 or 600 MHz. Multiplet groups having a pH dependent chemical shift in the physiological range are indicated by an asterisk.

 

Compound

Group

Shift (ppm) in H2O

Shift (ppm) in D2O

Multi-plicity

J (Hz)

Connectivity

 

Acetate

2CH3 *

1.9040

1.9030

s

None

Description: image002

NAA

 

Description: image004

Acetyl moiety

2CH3

2.0080

2.0050

s

Aspartate moiety

2CH

4.3817

4.3823

dd

3.861

2-3

3CH2

2.6727

2.6759

dd

9.821

2-3'

2.4863

2.4866

dd

-15.592

3-3'

NH

7.8205

7.8155

d

6.400

NH-2

NAAGa

 

 

Description: image006

Acetyl moiety

2CH3

2.042

s

None

Aspartyl moiety

2CH

4.607

dd

4.412

2-3

3CH2

2.721

dd

9.515

2-3'

2.519

dd

-15.910

3-3'

Glutamate moiety

2CH

4.128

dd

3CH2

1.881

m

2.049

m

4CH2

2.190

m

2.180

 

ATPb

 

 

Description: image012

Ribose moiety

1¢CH

6.126 ¥

6.129

d

5.7

1¢-2¢

2¢CH

4.796

t

5.3

2¢-3¢

3¢CH

4.616

dd

3.8

3¢-4¢

4¢CH

4.396

qu

3.0

4¢-5¢

5¢,5¢¢CH2

4.295

m

3.1

4¢-5¢¢

4.206

m

-11.8

5¢-5¢¢

1.9

4¢-P

6.5

5¢-P

4.9

5¢¢-P

Adenosine moiety

2CH

8.224 ¥

8.234

s

8CH

8.514 ¥

8.522

s

NH2

6.755 ¥

s

Alanine

2CH

3.7746

3.7680

q

7.234

2-3

Description: image014

3CH3

1.4667

1.4655

d

-14.366

3-3', 3''

-14.366

3'-3''

GABA

2CH2

3.0128

3.0082

m

5.372

2-3

 

 

Description: image018

7.127

2-3'

3CH2

1.8890

1.8888

qu

10.578

2'-3

6.982

2'-3'

4CH2

2.2840

2.2828

t

7.755

3-4

7.432

3-4'

6.173

3'-4

7.933

-12.021

-13.121

-10.744

3'-4'

2-2’

3-3’

4-4’

Aspartate

2CH

3.8914

3.8867

dd

3.647

2-3

Description: image020

3CH2

2.8011

2.8021

dd

9.107

2-3'

2.6533

2.6508

dd

-17.426

3-3'

Choline

N(CH3)3

3.1850

3.1890

s

None

 

Description: image024

1CH2

4.0540

4.0500

m

3.140

1-2

2CH2

3.5010

3.5060

m

6.979

1-2'

3.168

1'-2'

7.011

1'-2

2.572

1-N

2.681

1'-N

0.57

-14.100

-14.070

N-CH3

1-1’

2-2’

Creatine

N(CH3)

3.0270

3.0260

s

None

Description: image026

2CH2

3.9130

3.9110

s

None

NH

6.6490

s

None

Ethanolamine

1CH2

3.8184

m

3.897

1-2

 

Description: image028

2CH2

3.1467

m

6.794

1-2'

6.694

1'-2

3.798

1'-2'

0.657

1-N

0.142

-10.640

-11.710

1'-N

1-1’

2-2’

D-Glucosec

 

 

Description: image035

           a-anomer

1CH

5.216

d

3.8

1-2

2CH

3.519

dd

9.6

2-3

3CH

3.698

t

9.4

3-4

4CH

3.395

t

9.9

4-5

5CH

3.822

m

1.5

5-6

6CH

3.826

dd

6.0

5-6'

CH

3.749

dd

-12.1

6-6'

b-anomer

1CH

4.630

d

8.0

1-2

2CH

3.230

dd

9.1

2-3

3CH

3.473

t

9.4

3-4

4CH

3.387

t

8.9

4-5

5CH

3.450

m

1.6

5-6

6CH

3.882

dd

5.4

5-6'

CH

3.707

dd

-12.3

6-6'

Glutamate

2CH

3.7433

3.7444

dd

7.331

2-3

 

Description: image036

3CH2

2.0375

2.0424

m

4.651

2-3'

2.1200

2.1206

-14.849

3-3'

4CH2

2.3378

2.3354

m

8.406

3-4'

2.3520

2.3507

6.875

3'-4'

6.413

3-4

8.478

3'-4

-15.915

4-4'

Glutamine

2CH

3.7530

3.7625

t

5.847

2-3

 

Description: image038

3CH2

2.1290

2.1360

m

6.500

2-3'

2.1090

2.1180

-14.504

3-3'

4CH2

2.4320

2.4350

m

9.165

3-4

2.4540

2.4570

6.347

3-4'

6.324

3'-4

9.209

3'-4'

-15.371

4-4'

NH2

6.8160

s

7.5290

s

Glutathioned

 

Description: image042

Glycine moiety

10CH2

3.769

s

9NH

7.154

t

Cysteine moiety

7CH

4.5608

dd

7.09

7-7'

7'CH2

2.9264

dd

4.71

7-7''

2.9747

dd

-14.06

7'-7''

6NH

8.1770

d

Glutamate moiety

2CH

3.769

t

6.34

2-3

3CH2

2.159

m

6.36

2-3'

2.146

m

-15.48

3-3'

4CH2

2.510

m

6.7

3-4

2.560

m

7.6

3-4'

7.6

3'-4

6.7

3'-4'

-15.92

4-4'

Glycerol

1CH2

3.5522

3.5486

dd

-11.715

1-1', 3-3'

Description: image044

3.6402

3.6364

dd

4.427

1-2, 2-3

2CH

3.7704

3.7680

m

6.485

1'-2, 2-3'

3CH2

3.5522

3.5486

dd

3.6402

3.6363

dd

Glycero-phosphocholinee

 

Description: image047

Glycerol moiety

1CH2

3.605

dd

5.77

1-2, 2-3

3.672

dd

4.53

1'-2, 2-3'

2CH

3.903

m

3CH2

3.871

m

-14.780

1-1’, 3-3’

3.946

m

-9.320

7-7’, 8-8’

Choline moiety

7CH2

4.312

m

3.10

7-8, 7'-8'

2.67

7,7'-N

8CH2

3.659

m

5.90

7-8', 7'-8

N(CH3)3

3.212

s

6.03

3,3'-P; 7,7'-P

Glycine

2CH2

3.5480

3.5450

s

None

Description: image051

Histamine

aCH2

2.9813

3.0320

m

-16.120

a-a'

 

Description: image053

2.9897

3.0420

6.270

a'-b'

bCH2

3.2916

3.3148

t

8.147

a-b'

7.001

a'-b

6.868

a-b

-14.145

b-b'

Imidazole ring

  2CH *

7.8520

8.0250

d

1.07

2-1NH

  5CH *

7.0940

7.1620

m

1.19

5-1NH

0.73

5-b,b'

Histidine

aCH

3.9752

3.9959

dd

7.959

a-b

Description: image057

bCH2

3.1195

3.1866

dd

4.812

a-b'

3.2212

3.2644

dd

-15.513

b-b'

Imidazole ring

  2CH *

7.7910

7.9010

d

1.07

2-1NH

  5CH *

7.0580

7.1030

m

1.20

5-1NH

0.72

5-b,b'

Homocarnosinee

aCH

4.472

m

6.88

a-NH

 

Description: image059

bCH2

3.185

dd

3.003

dd

Imidazole ring

  2CH *

7.075

s

  5CH *

8.081

d

GABA moiety

2CH2

2.962

m

3CH2

1.891

m

4CH2

2.367

m

7.899

d

NH3

6.397

s

myo-Inositol

1CH

3.5217

3.5177

dd

2.889

1-2

Description: image063

2CH

4.0538

4.0488

t

9.998

1-6

3CH

3.5217

3.5177

dd

3.006

2-3

4CH

3.6144

3.6114

t

9.997

3-4

5CH

3.2690

3.2652

t

9.485

4-5

6CH

3.6144

3.6114

t

9.482

5-6

scyllo-Inositol

1-6CH

3.3400

3.3340

s

None

Description: image065

Lactate

2CH

4.0974

4.0908

q

6.933

2-3

Description: image069

3CH3

1.3142

1.3125

d

Phenylalanine

aCH

3.9753

3.9829

dd

5.209

a-b

 

Description: image071

bCH2

3.2734

3.2827

dd

8.013

a-b'

3.1049

3.1132

dd

-14.573

b-b'

Phenyl ring

2CH

7.3223

7.3223

m

7.909

2-3

3CH

7.4201

7.4201

m

1.592

2-4

4CH

7.3693

7.3693

m

7.204

3-4

5CH

7.4201

7.4201

m

0.493

2-5

6CH

7.3223

7.3223

m

0.994

3-5

7.534

4-5

1.419

2-6

0.462

3-6

0.970

4-6

7.350

5-6

Phosphocreatine

N(CH3)

3.0290

3.0280

s

None

Description: image075

2CH2

3.9300

3.9260

s

None

NH

 6.5810 e

s

None

NH

 7.2960 e

s

None

Phosphoryl-

1CH2

4.2805

4.2851

m

2.284

1-2

 

Description: image077

choline

7.231

1-2'

2.235

1'-2'

7.326

1'-2

2CH2

3.6410

3.6440

m

2.680

1-N

2.772

1'-N

6.298

-14.890

-14.190

1-P

1-1’

2-2’

N(CH3)3

3.2080

3.2100

s

6.249

1'-P

Phosphoryl-

1CH2

3.9765

3.9825

m

3.182

1-2

 

Description: image081

ethanolamine

7.204

1'-2

6.716

1-2'

2.980

1'-2'

2CH2

3.2160

3.2150

m

7.288

1-P

7.088

1'-P

0.464

1-N

0.588

-14.560

-14.710

1'-N

1-1’

2-2’

Pyruvate

3CH3

2.3590

2.3550

s

None

Description: image083

Serine

2CH

3.8347

3.8349

dd

5.979

2-3

Description: image087

3CH2

3.9379

3.9352

dd

3.561

2-3'

3.9764

3.9764

dd

-12.254

3-3'

Succinate

2CH2

2.3920

2.3970

s

None

Description: image089

3CH2

2.3920

2.3970

s

None

Taurine

1CH2

3.4206

3.4190

t

6.742

1-2

 

Description: image093

6.403

1'-2

2CH2

3.2459

3.2473

t

6.464

1-2'

6.792

-12.438

-12.930

1'-2'

1-1’

2-2’

Threonine

2CH

3.5785

3.5784

d

4.917

2-3

Description: image095

3CH

4.2464

4.2444

m

6.350

3-4

4CH3

1.3158

1.3169

d

Tryptophan

aCH

4.0468

4.0483

dd

4.851

a-b

 

Description: image099

bCH2

3.4739

3.4787

dd

8.145

a-b'

3.2892

3.2949

dd

-15.368

b-b'

Indole ring

2CH

7.3120

7.3112

s

None

4CH

7.7260

7.7255

d

7.600

4-5

5CH

7.2788

7.2759

t

1.000

4-6

6CH

7.1970

7.1934

t

7.507

5-6

7CH

7.5360

7.5315

d

0.945

4-7

1.200

5-7

7.677

6-7

Tyrosine

aCH

3.9281

3.9299

dd

5.147

a-b

 

Description: image101

bCH2

3.1908

3.1965

dd

7.877

a-b'

3.0370

3.0434

dd

-14.726

b-b'

Phenyl ring

2CH

7.1852

7.1880

m

7.981

2-3

3CH

6.8895

6.8916

m

0.311

2-5

5CH

6.8895

6.8916

m

2.445

3-5

6CH

7.1852

7.1880

m

2.538

2-6

0.460

3-6

8.649

5-6

Valine

2CH

3.5953

3.5954

d

4.405

2-3

Description: image105

3CH

2.2577

2.2622

m

6.971

3-4

4CH3

1.0271

1.0290

d

7.071

3-4'

4'CH3

0.9764

0.9793

d

 

a Chemical shifts and coupling constants for these compounds were measured from the conventional 1D and 2D E.COSY (for NAAG only) spectra, and the values were not optimized.

b From reference(1); data acquired at 35°C, the solution pH was neutral (between 7 and 8) and the chemical shift reference used was DSS. Multiplicity given here was observed at 250 MHz. ¥This list also includes values obtained from our measurements, for data acquired at 600 MHz.

c From reference(2); data acquired at 25°C and the sample pH not known. Multiplicity given here was observed at 270 MHz.

d Coupling constants for Glutathione were measured from its 2D E.COSY spectra acquired at 500 MHz, and were optimized only for the cystine moiety.

e These two NH resonances are from –C=NH- and –NH-P- protons; however, no specific assignments have been made.

 

References

1.         Son TD, Chachaty C. Proton NMR and spin lattice relaxation study of nucleoside di- and triphosphates in neutral aqueous solutions. Biochim Biophys Acta 1977;500:405-418.

2.         Perkins SJ, Johnson LN, Philips DC. High-resolution 1H- and 13C-N.M.R. spectra of D-glucopyranose, 2-acetamido-2-deoxy-D-glucopyranose, and related compounds in aqueous media. Carbohydr Res 1977;59:19-34.

 

Related articles

This work provides the basis for computer simulation of NMR spectra, which we have used for spectral analysis and optimization of acquisition parameters. Publications describing this work include:

1.         Young K, Govindaraju V, Soher BJ, Maudsley AA. Automated spectral analysis I:  Formation of a priori information by spectral simulation. Magn Reson Med 1998;40:812-815.

2.         Young K, Soher BJ, Maudsley AA. Automated spectral analysis II: Application of wavelet shrinkage for characterization of non-parameterized signals. Magn Reson Med 1998;40:816-821.

3.         Soher BJ, Young K, Govindaraju V, Maudsley AA. Automated spectral analysis III: Application to in vivo proton MR spectroscopy and spectroscopic imaging. Magn Reson Med 1998;40:822-831.

4.         Young K, Matson GB, Govindaraju V, Maudsley AA. Spectral simulations incorporating gradient coherence selection. J Magn Reson 1999;140:146-152.

5.         Govindaraju V, Young K, Matson GB, Maudsley AA. Optimization of acquisition sequence parameters by spectral simulation. Submitted 2000;

 

Acknowledgements

Copyright of the published article is maintained by John Wiley and Sons, Chichester, New York.

This work was supported by NIH grant, R01AG12119, and the work carried out at the University of California San Francisco, and the VA Medical center San Francisco.

 

Last Updated: 06/22/2007