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Cited by 1,049

The DOI matches its Crossref record; 17 of the 17 references it cites were found in a registry or an index.

In situ neutralization in Boc‐chemistry solid phase peptide synthesis: Rapid, high yield assembly of difficult sequences

SCHNölzer, MARTINA, ALEWOOD, PAUL, JONES, ALUN, ALEWOOD, DIANNE, KENT, STEPHEN B.H.·1992·International Journal of Peptide and Protein Research
DOI 10.1111/j.1399-3011.1992.tb00291.x
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Abstract

Simple, effective protocols have been developed for manual and machine‐assisted Boc‐chemistry solid phase peptide synthesis on polystyrene resins. These use in situ neutralization [i.e. neutralization simultaneous with coupling], high concentrations (> 0.2 M) of Boc‐amino acid‐OBt esters plus base for rapid coupling, 100% TFA for rapid Boc group removal, and a single short (30 s) DMF flow wash between deprotection/coupling and between coupling/deprotection. Single 10 min coupling times were used throughout. Overall cycle times were 15 min for manual and 19 min for machine‐assisted synthesis (75 residues per day). No racemization was detected in the base‐catalyzed coupling step. Several side reactions were studied, and eliminated. These included: pyrrolidonecarboxylic acid formation from Gln in hot TFA‐DMF; chain‐termination by reaction with excess HBTU; and, chain termination by acetylation (from HOAc in commercial Boc‐amino acids). The in situ neutralization protocols gave a significant increase in the efficiency of chain assembly, especially for “difficult” sequences arising from sequence‐dependent peptide chain aggregation in standard (neutralization prior to coupling) Boc‐chemistry SPPS protocols or in Fmoc‐chemistry SPPS. Reported syntheses include HIV‐1 protease(1–50,Cys.amide), HIV‐1 protease(53–99), and the full length HIV‐1 protease(1–99).

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Citations

Cites

Show all 17 references

Research works printed but not linked: 28

  1. Alewood P., 1991, Peptides, 174
  2. Kent S.B.H., 1992, Innovation and Perspectives in Solid Phase Synthesis II
  3. Mapelli C., 1991, Peptides, 316
  4. Larsen B., 1992, Innovation and Perspectives in Solid Phase Synthesis II
  5. Young J.D., 1990, Peptide Res., 3, 194
  6. 10.1007/978-94-011-2264-1_192 · doi:10.1007/978-94-011-2264-1_192
  7. Gausepohl H., 1992, Innovation and Perspectives in Solid Phase Synthesis II
  8. 10.1007/978-94-011-2264-1_281 · doi:10.1007/978-94-011-2264-1_281
  9. Larsen B., 1991, Peptides, 183
  10. 10.1007/978-94-011-2264-1_231 · doi:10.1007/978-94-011-2264-1_231
  11. Nakaie C.R., 1990, Peptides, 1022
  12. 10.1111/j.1399-3011.1989.tb01576.x · doi:10.1111/j.1399-3011.1989.tb01576.x
  13. Gausepohl H., 1992, Innovation and Perspectives in Solid Phase Synthesis
  14. Briand J.P., 1991, Peptides, 80
  15. Fields G.B., 1990, Innovation and Perspectives in Solid Phase Synthesis, 241
  16. 10.1111/j.1399-3011.1991.tb00737.x · doi:10.1111/j.1399-3011.1991.tb00737.x
  17. 10.1039/p19850001025 · doi:10.1039/p19850001025
  18. Kent S.B.H., 1991, Peptides, 172
  19. 10.1007/978-94-010-9595-2_49 · doi:10.1007/978-94-010-9595-2_49
  20. Henklein P., 1992, Innovation and Perspectives in Solid Phase Synthesis
  21. 10.1007/978-94-011-2264-1_201 · doi:10.1007/978-94-011-2264-1_201
  22. Schnölzer M., 1992, Anal. Biochem.
  23. 10.1021/jo00263a016 · doi:10.1021/jo00263a016
  24. 10.1111/j.1399-3011.1983.tb02068.x · doi:10.1111/j.1399-3011.1983.tb02068.x
  25. 10.1016/0003-2697(89)90068-7 · doi:10.1016/0003-2697(89)90068-7
  26. Jezek J., 1990, Peptides, 74
  27. Kent S.B.H., 1984, Peptides 1984, 185
  28. Schnölzer M., 1992, Peptides, Proceedings of the 12th American Peptide Symposium, 623

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Metadata

Authors
SCHNölzer, M., ALEWOOD, P., JONES, A., ALEWOOD, D., & KENT, S. B. H.
Venue
International Journal of Peptide and Protein Research
Publisher
Wiley
Published
1992-09
Volume
40
Issue
3-4
Pages
180-193
ISSN
0367-8377 (ISSN-L)
DOI
10.1111/j.1399-3011.1992.tb00291.x
OpenAlex
W2146837416
Cited by
1,049
References
17
FWCI
2.80
Type
journal article
Language
en
Open access
closed
Licence
onlinelibrary.wiley.com/termsAndConditions#vor (vor, 5977 d)

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CoChat. (2026). Citation check: In situ neutralization in Boc‐chemistry solid phase peptide synthesis: Rapid, high yield assembly of difficult sequences. https://app.cochat.ai/papers/10.1111/j.1399-3011.1992.tb00291.x
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SCHNölzer, M., ALEWOOD, P., JONES, A., ALEWOOD, D., & KENT, S. B. H. (1992). In situ neutralization in Boc‐chemistry solid phase peptide synthesis: Rapid, high yield assembly of difficult sequences. International Journal of Peptide and Protein Research. https://doi.org/10.1111/j.1399-3011.1992.tb00291.x

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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).

Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.