The DOI matches its Crossref record.
4‐Dimethylamino‐3‐butyn‐2‐one as Activating Agent for Peptide Synthesis
Abstract
Very high yields, mild conditions, and no racemization are characteristic of peptide syntheses utilizing (1). R—COOH is an N-protected amino acid, R′—NH2 is an amino ester or similar species. The procedure can also be applied to R—COOH with unprotected side chain functions.
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The rate-limiting step of the aminolysis process is closely related to the basicity of the attacking amine and the nature of the leaving group, as measured by the Brönsted parameter β.
“The rate-limiting step of the aminolysis process is closely related to the basicity of the attacking amine and the nature of the leaving group, as measured by the Brönsted parameter β (defined as the slope in plots of log k vs pKa).31”
From Ynamide Coupling Reagents: Origin and Advances (2024) · cites this paper as [31]
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No references could be resolved yet.
Research works printed but not linked: 12
- 10.1002/ange.19780900408 · DOI
- 10.1002/anie.197802671 · DOI
- 10.1016/S0040-4020(01)82192-X · DOI
- 10.1021/jo01261a056 · DOI
- 10.1021/jo00826a020 · DOI
- 10.1016/S0040-4020(01)92755-3 · DOI
- 10.1021/ja01091a057 · DOI
- Williams M. W., J. Chem. Soc., 1964, 3701
- Williams M. W., J. Chem. Soc., 1963, 881
- 10.1021/ja00958a058 · DOI
- 10.1021/ja00995a032 · DOI
- 10.1021/ja01544a077 · DOI
Cited by
Sorted by citations
Ynamide Coupling Reagents: Origin and Advances
Hu, L., & Zhao, J. (2024) · Accounts of Chemical Research · doi:10.1021/acs.accounts.3c00743 · Cited by 89
“Later, Gais 25 and Neuenschwander, 26 independently, anchored an electron-withdrawing group (EWG) to the C − C triple bond to stabilize ynamine by taking advantage of the electron push − pull effect.”
Background
Metadata
- Authors
- Gais, H.
- Affiliations
- Technische Universität Darmstadt (DE)
- Corresponding author
- Gais, Hans‐Joachim
- ORCID
- Gais, Hans‐Joachim
- Venue
- Angewandte Chemie International Edition in English
- Publisher
- Wiley
- Published
- 1978-08
- Volume
- 17
- Issue
- 8
- Pages
- 597-598
- ISSN
- 0570-0833 (ISSN-L)
- OpenAlex
- W2062757536
- Cited by
- 19
- References
- 0
- Citations by year
- 2026: 5 · 2025: 1 · 2024: 1 · 2023: 1 · 2017: 1 · 2016: 1
- FWCI
- 0.00
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Angewandte Chemie International Edition in English (publishedVersion)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Synthesis and Analysis
- Physical Sciences › Chemistry › Organic Chemistry › Organic Chemistry Synthesis Methods
- Physical Sciences › Chemistry › Organic Chemistry › Advanced Synthetic Organic Chemistry
- Keywords
- peptide synthesis, activating agents, N-protected amino acids, amino esters, racemization prevention, side-chain protection, peptide bond formation
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