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Reductive amination of carbohydrates using NaBH(OAc)3

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Abstract

An improved protocol for reductive amination of carbohydrates is developed. This derivatization facilitates the detection of oligosaccharides in HPLC-UV and mass spectrometric applications by enhancing the signal of the carbohydrates. In this study, reductive amination was achieved using NaBH(OAc)3.This reducing agent is an attractive alternative to the toxic, but extensively used reducing agent, NaBH3CN. Several types of carbohydrates were successfully derivatized using NaBH(OAc)3, and the results obtained from this protocol were compared with those obtained with NaBH3CN. Both reducing agents were equally effective in side-by-side analysis. Two purification strategies (purification by zip-tip and HPLC) were implemented and the instrumental limit of detection of each method was compared. The detection limit was ~1,000 times lower when the purification was done using HPLC, compared to using the zip-tip. Since the derivatization by-products in this protocol are not toxic, MS analysis also could also be performed directly, without purification. The MS/MS data of derivatized and underivatized oligosaccharides were acquired as well. The derivatized oligosaccharides produce more easily interpretable product ions than underivatized oligosaccharides.

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References

  1. Dwek RA (1996) Chem Rev 96:683–720

    Article  Google Scholar 

  2. Lindhorst TK (ed) (2003) Essentials of carbohydrate chemistry, 2nd edn. Wiley-VCH, Weinheim

    Google Scholar 

  3. Osborn HMI, Khan TH (eds) (2000) Oligosaccharides: their synthesis and biological roles. Oxford University Press, New York

  4. Zaia J (2004) Mass Spectrom Rev 23:161–227

    Article  Google Scholar 

  5. De Hoffman E, Stroobant V (eds) (2001) Mass spectrometry: principles and applications, 2nd edn. Wiley, London

    Google Scholar 

  6. Dell A, Carman NH, Tiller PR, Thomas-Oates JE (1988) Biomed Environ Mass Spectrom 16:19–24

    Google Scholar 

  7. Harvey DJ (2000) J Am Soc Mass Spectrom 11:900–915

    Article  Google Scholar 

  8. Takao T, Tambara Y, Nakamura A, Yoshino K, Fukuda H, Fukuda M, Shimonishi Y (1996) Rapid Commun Mass Spectrom 10:677–640

    Article  Google Scholar 

  9. Okamoto M, Takahashi K, Doi T (1995) Rapid Commun Mass Spectrom 9:641–643

    Google Scholar 

  10. Harvey DJ (2000) Rapid Commun Mass Spectrom 14:862–871

    Article  Google Scholar 

  11. Wu W, Hamase K, Kiguchi M, Yamamoto K, Zaitsu K (2000) Anal Sci 16:919–922

    Google Scholar 

  12. Yoshino K, Takao T, Murata H, Shimonishi Y (1995) Anal Chem 67:4028–4031

    Google Scholar 

  13. Hase S, Ibuki T, Ikenaka T (1984) J Biochem 95:197–203

    Google Scholar 

  14. Okamoto M, Takahashi K, Doi T, Takimoto Y (1997) Anal Chem 69:2919–2926

    Article  Google Scholar 

  15. Mo W, Takao T, Sakamoto H, Shimonishi Y (1998) Anal Chem 70:4520–4526

    Google Scholar 

  16. Harvey DJ (2000) Analyst 125:609–617

    Article  Google Scholar 

  17. Bigge JC, Patel T P, Bruce JA, Goulding PN, Charles SM, Parekh RB (1995) Anal Biochem 230:229–238

    Article  Google Scholar 

  18. Franz AH, Molinski TF, Lebrilla CB (2001) J Am Soc Mass Spectrom 12:1254–1261

    Article  Google Scholar 

  19. Che FY, Song JF, Zeng R, Wang KY, Xia QC (1999) J Chromatogr A 858:229–238

    Article  Google Scholar 

  20. Shen X, Perreault H (1999) J Mass Spectrom 34:502–510

    Article  Google Scholar 

  21. Camilleri P, Tolson D, Birrell H (1998) Rapid Commun Mass Spectrom 12:144–148

    Article  Google Scholar 

  22. Okafo G, Burrow L, Carr, SA, Roberts GD, Johnson W, Camilleri P (1996) Anal Chem 68:4424–4430

    Article  Google Scholar 

  23. Kiguchi M, Hamase K, Wu W, Yamamoto K, Zaitsu K (1999) Anal Sci 15:903–905

    Google Scholar 

  24. Drummond KJ, Yates EA, Turnbull JE (2001) Proteomics 1:304–310

    Article  Google Scholar 

  25. Prime SB, Shipston NF, Merry TH (1997) Biomethods 9:235–260

    Google Scholar 

  26. Jiang H, Butnev VY, Bousfield GR, Desaire H (2004) J Am Soc Mass Spectrom 15:750–758

    Article  Google Scholar 

  27. Domon B, Costello CE (1988) Glycoconjugate J 5:397–409

    Article  Google Scholar 

Download references

Acknowledgements

The authors would like to thank the National Institute of Health for funding project number 1 P20 RR17708-01.

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Authors and Affiliations

  1. Department of Chemistry, University of Kansas, Lawrence, KS, 66045, USA

    Dilusha S. Dalpathado, Hui Jiang, Marcus A. Kater & Heather Desaire

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  1. Dilusha S. Dalpathado
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  2. Hui Jiang
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  3. Marcus A. Kater
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  4. Heather Desaire
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Correspondence to Heather Desaire.

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Dalpathado, D.S., Jiang, H., Kater, M.A. et al. Reductive amination of carbohydrates using NaBH(OAc)3. Anal Bioanal Chem 381, 1130–1137 (2005). https://doi.org/10.1007/s00216-004-3028-9

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  • DOI: https://doi.org/10.1007/s00216-004-3028-9

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