The DOI matches its Crossref record.
Mechanism of Amide Formation by Carbodiimide for Bioconjugation in Aqueous Media
Abstract
To study the mechanism of amide formation between carboxylic acid and amine in aqueous media using 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride (EDC), hydrogels with two different types of carboxyl group locations were employed as substrates containing the carboxylic acid, while ethylenediamine and benzylamine were used as amine. In parallel, a study was undertaken with cyclizable carboxylic acids (maleic acid and poly(acrylic acid) and noncyclizable carboxylic acids (fumaric acid and poly(ethylene glycol) with the terminal carboxyl groups) to assess the reaction products by 13C-NMR and IR. EDC rapidly lost its activity in aqueous media of low pH, producing the corresponding urea derivative, but was very stable at neutral and higher pH regions. EDC could react with carboxyl groups at a relatively narrow low pH range such as 3.5-4.5. If carboxyl groups were cyclizable, they would react quickly with EDC producing carboxylic anhydrides, which formed the corresponding amides when amine compounds were present. On the other hand, a trace of amide was formed in the case of noncyclizable carboxylic acids. In addition, an excess of EDC caused an undesired side reaction to form stable N-acylurea, regardless of the special location of carboxylic acids.
Overview
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Verification
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
Citations
Cited by
Pieper, J. S., Hafmans, T., Veerkamp, J. H., & van Kuppevelt, T. H. (2000) · Biomaterials · doi:10.1016/s0142-9612(99)00222-7 · Cited by 323
Engineering Hydrogel Adhesion for Biomedical Applications via Chemical Design of the Junction
Bovone, G., Dudaryeva, O. Y., Marco-Dufort, B., & Tibbitt, M. W. (2021) · ACS Biomaterials Science & Engineering · doi:10.1021/acsbiomaterials.0c01677 · Cited by 298
Delgado, L. M., Bayon, Y., Pandit, A., & Zeugolis, D. I. (2015) · Tissue Engineering Part B: Reviews · doi:10.1089/ten.teb.2014.0290 · Cited by 272
Kang, S., Park, J. B., Lee, T.-J., Ryu, S., Bhang, S. H., La, W.-G., Noh, M.-K., Hong, B. H., & Kim, B.-S. (2015) · Carbon · doi:10.1016/j.carbon.2014.11.029 · Cited by 125
Kulkarni, G., Guha Ray, P., Byram, P. K., Kaushal, M., Dhara, S., & Das, S. (2020) · International Journal of Biological Macromolecules · doi:10.1016/j.ijbiomac.2020.09.016 · Cited by 40
Metadata
- Authors
- Nakajima, N., & Ikada, Y.
- Venue
- Bioconjugate Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1995-01-01
- Volume
- 6
- Issue
- 1
- Pages
- 123-130
- ISSN
- 1043-1802 (ISSN-L)
- 1520-4812
- OpenAlex
- W2058120775
- Cited by
- 777
- References
- 0
- FWCI
- 1.42
- Type
- journal article
- Language
- en
- Open access
- closed
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
How to cite
Cite CoChat for the checks on this page, and the paper for its own findings.
- This page
- CoChat. (2026). Citation check: Mechanism of Amide Formation by Carbodiimide for Bioconjugation in Aqueous Media. https://app.cochat.ai/papers/10.1021/bc00031a015
- The paper
- Nakajima, N., & Ikada, Y. (1995). Mechanism of Amide Formation by Carbodiimide for Bioconjugation in Aqueous Media. Bioconjugate Chemistry. https://doi.org/10.1021/bc00031a015
Data sources
Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
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.
