Glycine N-carboxyanhydride

Glycine N-carboxyanhydride is an organic compound with the formula HNCH(CO)2O. A colorless solid, it is the product of the phosgenation of glycine.[4][5] Glycine N-carboxyanhydride is the simplest member of the amino acid N-carboxyanhydrides. It is also the parent of the 2,5-oxazolidinedione family of heterocycles.

Glycine N-carboxyanhydride
Names
Preferred IUPAC name
1,3-Oxazolidine-2,5-dione
Other names
glycine N-carboxyanhydride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.016.882
EC Number
  • 218-570-6
UNII
  • InChI=1S/C3H3NO3/c5-2-1-4-3(6)7-2/h1H2,(H,4,6)
    Key: ARAFEULRMHFMDE-UHFFFAOYSA-N
  • C1C(=O)OC(=O)N1
Properties
C3H3NO3
Molar mass 101.061 g·mol−1
Appearance white solid
Density 1.74 g/cm3[1]
Melting point 96–98[2] °C (205–208 °F; 369–371 K)
Hazards
GHS labelling:[3]
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H315, H318, H335
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P332+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Other derivatives

2,5-Oxazolidinediones can also be prepared from Schiff base derivatives of amino acids.[6]

See also

References
  1. Kanazawa, Hitoshi; Matsuura, Yoshiki; Tanaka, Nobuo; Kakudo, Masao; Komoto, Tadashi; Kawai, Tohru (1976). "The Crystal and Molecular Structure ofN-Carboxy Anhydride of Glycine". Bulletin of the Chemical Society of Japan. 49 (4): 954–956. doi:10.1246/bcsj.49.954.
  2. Wilder, Renee; Mobashery, Shahriar (1992). "The use of triphosgene in preparation of N-carboxy .alpha.-amino acid anhydrides". The Journal of Organic Chemistry. 57 (9): 2755–2756. doi:10.1021/jo00035a044.
  3. "Oxazolidine-2,5-dione". pubchem.ncbi.nlm.nih.gov. Retrieved 5 April 2022.
  4. Kricheldorf HR (September 2006). "Polypeptides and 100 years of chemistry of alpha-amino acid N-carboxyanhydrides". Angewandte Chemie. 45 (35): 5752–84. doi:10.1002/anie.200600693. PMID 16948174.
  5. Tian ZY, Zhang Z, Wang S, Lu H (October 2021). "A Moisture-Tolerant Route to Unprotected α/β-Amino Acid N-carboxyanhydrides and Facile Synthesis of Hyperbranched Polypeptides". Nature Communications. 12 (1): 5810. Bibcode:2021NatCo..12.5810T. doi:10.1038/s41467-021-25689-y. PMC 8490447. PMID 34608139.
  6. Sucu BO, Ocal N, Erden I (2015). "Direct synthesis of imidazolidin-4-ones via cycloadditions of imines with a Leuchs' anyhdride". Tetrahedron Letters. 56 (20): 2590–2. doi:10.1016/j.tetlet.2015.04.002.
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