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H-L-AllylGly-OH
Chemical name: (S)-Allylglycine (>98%, >99%ee) // Synonyms: (S)-2-Aminopent-4-enoic acid, 4,5-Dehydro-L-norleucine (>98%, >99%ee), H-AllylGly-OH
- Product code:HAA7320
- CAS No.:16338-48-0
- Formula:C5H9NO2
- Molecular weight:115.13 g/mol
Starting at $910.00
description
Allylglycine is a glycine derivative. It is an inhibitor of the enzyme glutamate decarboxylase.[1]
Inhibition of glutamate decarboxylase blocks GABA biosynthesis, leading to lower levels of the neurotransmitter.[2] It is used to induce convulsions in animals in scientific studies.
N-Allyloxycarbonyl (Alloc) are widely used protecting groups, i.e. for amines and amino acids, as they are quantitatively andvery rapidly converted to free amino compounds by palladium. Deprotection of allyl (All) carboxylates and allyl aryl ethers can also be carried out accordingly.
All and Alloc are fully compatible with Fmoc/tBu and Boc/Bzl strategies, as well as with Z protecting groups.
references
[1] Abshire VM, Hankins KD, Roehr KE, DiMicco JA (November 1988). "Injection of L-allylglycine into the posterior hypothalamus in rats causes decreases in local GABA which correlate with increases in heart rate". Neuropharmacology 27 (11): 1171-7. doi:10.1016/0028-3908(88)90013-5. PMID 3205383.
[2] Sajdyk T, Johnson P, Fitz S, Shekhar A (August 2008). "Chronic inhibition of GABA synthesis in the bed nucleus of the stria terminalis elicits anxiety-like behavior". J. Psychopharmacol. (Oxford) 22 (6): 633-41. doi:10.1177/0269881107082902. PMID 18308797.
Selective cleavage of the allyl and (allyloxy)carbonyl groups through palladium-catalyzed hydrostannolysis with tributyltin hydride. Application to theselective protection-deprotection of amino acid derivatives and in peptide synthesis; O. Dangles, F. Guibe, G. Balavoine, S. Lavielle and A. Marquet; The Journal of Organic Chemistry 1987; 52: 4984-4993. doi:10.1021/jo00231a027
Allylic protecting groups and their use in a complex environment part II: Allylic protecting groups and their removal through catalytic palladium π-allyl methodology; F. Guibé; Tetrahedron 1998; 54: 2967-3042. doi:http://dx.doi.org/10.1016/S0040-4020(97)10383-0
Mild non-transition metal catalyzed deprotection of N-allyloxycarbonyl amines; R. H. Szumigala Jr, E. Onofiok, S. Karady, J. D. Armstrong Iii and R. A. Miller; Tetrahedron letters 2005; 46: 4403-4405. doi:http://dx.doi.org/10.1016/j.tetlet.2005.04.064
Highly efficient removal of allyloxycarbonyl (Alloc) function provides a practical orthogonal protective strategy for carbohydrates; G. H. Zong, S. Q. Yan, X. M. Liang, J. J. Zhang, D. Q. Wang and F. Z. Kong; Chinese Chemical Letters 2009; 20: 127-130. doi:http://dx.doi.org/10.1016/j.cclet.2008.11.002
The Allyloxycarbonyl (Aloc) Moiety-Conversion of an Unsuitable into a Valuable Amino Protecting Group for Peptide Synthesis; H. Kunz and C. Unverzagt; Angewandte Chemie International Edition in English 1984; 23: 436-437. doi:10.1002/anie.198404361
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