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SOLID‐PHASE PEPTIDE SYNTHESIS USING MILD BASE CLEAVAGE OF NαFLUORENYLMETHYLOXYCARBONYLAMINO ACIDS, EXEMPLIFIED BY A SYNTHESIS OF DIHYDROSOMATOSTATIN
Abstract
N α‐9‐Fluorenylmethyloxycarbonyl (Fmoc) amino acids will be of advantage in solid phase peptide synthesis. The Fmoc‐group is quantitatively cleaved by mild base (piperidine). This permits the use of tert‐butyl‐type side chain blocking and of peptide‐to‐resin linkage cleavable by mild acidolysis. Side reactions arising from repetitive acid deprotection and final HF cleavage in contemporary solid phase synthesis are avoided. Fully bioactive and homogeneous dihydrosomatostatin was obtained in 53% overall yield.
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Cited by
Iwata, N., Tsubuki, S., Takaki, Y., Watanabe, K., Sekiguchi, M., Hosoki, E., Kawashima-Morishima, M., Lee, H.-J., Hama, E., Sekine-Aizawa, Y., et al. (2000) · Nature Medicine · doi:10.1038/72237 · Cited by 867
Advances in Fmoc solid‐phase peptide synthesis
Behrendt, R., White, P., & Offer, J. (2016) · Journal of Peptide Science · doi:10.1002/psc.2836 · Cited by 760
Solid-phase peptide synthesis: from standard procedures to the synthesis of difficult sequences
Coin, I., Beyermann, M., & Bienert, M. (2007) · Nature Protocols · doi:10.1038/nprot.2007.454 · Cited by 638
Histones: At the Crossroads of Peptide and Protein Chemistry
Müller, M. M., & Muir, T. W. (2015) · Chemical Reviews · doi:10.1021/cr5003529 · Cited by 247
Metadata
- Authors
- Chang, C., & Meienhofer, J.
- Venue
- International Journal of Peptide and Protein Research
- Publisher
- Wiley
- Published
- 1978-03
- Volume
- 11
- Issue
- 3
- Pages
- 246-249
- ISSN
- 0367-8377 (ISSN-L)
- OpenAlex
- W2008494805
- Cited by
- 304
- References
- 0
- FWCI
- 2.69
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: SOLID‐PHASE PEPTIDE SYNTHESIS USING MILD BASE CLEAVAGE OF NαFLUORENYLMETHYLOXYCARBONYLAMINO ACIDS, EXEMPLIFIED BY A SYNTHESIS OF DIHYDROSOMATOSTATIN. https://app.cochat.ai/papers/10.1111/j.1399-3011.1978.tb02845.x
- The paper
- Chang, C., & Meienhofer, J. (1978). SOLID‐PHASE PEPTIDE SYNTHESIS USING MILD BASE CLEAVAGE OF NαFLUORENYLMETHYLOXYCARBONYLAMINO ACIDS, EXEMPLIFIED BY A SYNTHESIS OF DIHYDROSOMATOSTATIN. International Journal of Peptide and Protein Research. https://doi.org/10.1111/j.1399-3011.1978.tb02845.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.
