Skip to main content
SpringerLink
Log in

Synthesis of novel sugar derived aziridines, as starting materials giving access to sugar amino acid derivatives

  • Original Article
  • Published:
Amino Acids Aims and scope Submit manuscript

Abstract

d-Erythrosyl aziridines were obtained from d-erythrosyl triazoles either by photolysis or through diazirine intermediates. These were found to undergo rich, high yielding chemistry by reaction with protic acids (HCl, BiI3/H2O and trifluoroacetic acid) leading to two types of furanoid sugar α-amino acids, and polyhydroxylprolines. Based on experimental evidence, reaction mechanisms have been proposed for the syntheses.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Scheme 1
Scheme 2
Scheme 3
Scheme 4
Scheme 5
Fig. 3
Scheme 6
Scheme 7
Scheme 8
Scheme 9
Scheme 10

Similar content being viewed by others

References

  • Alves MJ, Gilchrist TL (2009) Organic azides: syntheses and applications. In: Bräse S, Banert B (eds) Small rings by azide chemistry. Wiley, New York, pp 167–190 (ISBN: 978-0-470-51998-1)

    Google Scholar 

  • Asano N, Kato A, Miyauchi M, Kizu H, Kameda Y, Watson AA, Nash RJ, Fleet GWJ (1998) Nitrogen-containing furanose and pyranose analogues from hyacinthus orientalis. J Nat Prod 61:625–628

    Article  CAS  Google Scholar 

  • Bailey AD (2007) Green chemistry using bismuth salts bismuth (III) iodide catalyzed deprotection of acetals and ketals in H2O. Honors Projects, Paper 6

  • Bogdanova A, Popik VV (2003) Wavelength-dependent photochemistry of Diazo Meldrum’s acid and its spirocyclic isomer, Diazirino Meldrum’s acid: Wolff rearrangement versus isomerization. J Am Chem Soc 125:1456–1457

    Article  CAS  Google Scholar 

  • Chakraborty TK, Srinivasu P, Tapadar S, Mohan BK (2005) Sugar amino acids in designing new molecules. Glycoconj J 22(3):83–93

    Article  CAS  Google Scholar 

  • Chapleur Y (1998) Carbohydrate mimics: concepts and methods. Wiley-VCH, Weinheim

    Google Scholar 

  • Gruner SAW, Locardi E, Lohof E, Kessler H (2002) Carbohydrate-based mimetics in drug design: sugar amino acids and carbohydrate scaffolds. Chem Rev 102:491–514

    Article  CAS  Google Scholar 

  • Guang-Zong T, Xiao-Li W, Jing H, Xue-bin W, Xiao-Qiang G, Jian Y (2015) Recent progress of sugar amino acids: synthetic strategies and applications as glycomimetics and peptidomimetics. Chin Chem Lett, pp 922–930

  • Guptill DM, Cohen CM, Davies HML (2013) Rhodium(II)-catalyzed stereoselective synthesis of allylsilanes. Org Lett 15(24):6120–6123

    Article  CAS  Google Scholar 

  • Huisgen R (1963) 1,3-Dipolar cycloadditions. Past and future. Angew Chem Int Ed Eng 2:565–632

    Article  Google Scholar 

  • Isono K (1988) Nucleoside antibiotics: structure, biological activity and biosynthesis. J Antibiot 41:1711–1739

    Article  CAS  Google Scholar 

  • Isono K, Asahi K, Suzuki S (1969) Studies on polyoxins, antifungal antibiotics The structure of polyoxins. J Am Chem Soc 91(26):7490–7505

    Article  CAS  Google Scholar 

  • Li J, Li L, Feng C, Chen Y, Tan H (2012) Novel polyoxins generated by heterologously expressing polyoxin biosynthetic gene cluster in the sanN inactivated mutant of Streptomyces ansochromogenes. Microb Cell Fact 11:135

  • Liao G, Li J, Li L, Yang H, Tian Y, Tan H (2009) Selectively improving nikkomycin Z production by blocking the imidazolone biosynthetic pathway of nikkomycin X and uracil feeding in Streptomyces ansochromogenes. Microb Cell Fact 8:61–68

    Article  Google Scholar 

  • Malle BM, Lundt I, Tanja MW (2008) Regioselective intramolecular ring closure of 2-amino-6-bromo-2,6-dideoxyhexono-1,4-lactones to 5- or 6-membered iminuronic acid analogues: synthesis of 1-deoxymannojirimycin and 2,5-dideoxy-2,5-imino-d-glucitol. Organ Biomol Chem 6(10):1779–1786

    Article  CAS  Google Scholar 

  • Pino-González MS, Noé O (2008) Synthesis of intermediates in the formation of hydroxy piperidines and 2-azido lactones from d-erythrose. Tetrahedron Asymmetry 19(6):721–729

    Article  Google Scholar 

  • Risseeuw MDP, Overhand M, Fleet GWJ, Simone MI (2013) A compendium of sugar amino acids and their carbocyclic and heterocyclic nitrogen analogues. Amino Acids 45:613–689

    Article  CAS  Google Scholar 

  • Singh SG, D’hooghe M, De Kimpe N (2007) Synthesis and reactivity of C-heteroatom-substituted aziridines. Chem Rev 107:2080–2135

    Article  CAS  Google Scholar 

  • Sousa CEA, Ribeiro AMP, Fortes AG, Cerqueira NMFSA, Alves MJ (2017) Total facial discrimination of 1,3-dipolar cycloadditions in a d-erythrose 1,3-dioxane template: computational studies of a concerted mechanism. J Org Chem 82:982–991

    Article  CAS  Google Scholar 

  • Takeuchi Y, Marshall GR (1998) Conformational analysis of reverseturn constraints by N-methylation and N-hydroxylation of amide bonds in peptides and non-peptide mimetics. J Am Chem Soc 120(22):5363–5372

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We thank FCT for project funding PTDC/QEQ-MED/1671/2012; the NMR Portuguese network (PTNMR, Bruker Avance III 400-Univ. Minho), and FCT and FEDER (European Fund for Regional Development)-COMPETE-QREN-EU for financial support to CQ/UM.

Funding

This study was funded by Fundação para a Ciência e a Tecnologia (SFRH/BD/87292/2012).

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Minho, Gualtar, 4710-057, Braga, Portugal

    Cristina E. A. Sousa & Maria J. Alves

Authors
  1. Cristina E. A. Sousa
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Maria J. Alves
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Maria J. Alves.

Ethics declarations

Conflict of interest

The authors declare that there is no competing interests exist.

Consent for publication

The authors declare that there is no duality of interest associated with this manuscript, and all the authors consent to publish this manuscript.

Additional information

Handling editor: A. Jirgensons.

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary data Contains NMR spectra of all new compounds obtained. (PDF 13834 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sousa, C.E.A., Alves, M.J. Synthesis of novel sugar derived aziridines, as starting materials giving access to sugar amino acid derivatives. Amino Acids 53, 1123–1134 (2021). https://doi.org/10.1007/s00726-021-03017-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00726-021-03017-4

Keywords

Search

Navigation