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Fmoc-L-Aea-OH
Chemical name: (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-(1,3-dioxolan-2-yl)pentanoic acid // Synonyms: Fmoc-allysine ethylene acetal, Fmoc-Aea-OH
- Product code:FAA4390
- CAS No.:1234692-73-9
- Formula:C23H25NO6
- Molecular weight:411.45 g/mol
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description
A versatile derivative for the introduction of a highly reactive aldehyde functionality into a peptide side chain. This protected building block is compatible with Fmoc/tBu SPPS conditions and the cyclic actelal will cleave upon standard cleavage conditions with TFA/water and liberating the side chain aldehyde group. Allysine is produced naturally by the
action of lysyl oxidase on protein residues. Cross-links formed between the reaction of allysine and lysine and hydroxylysine residues are responsible for giving collagen fibrils their tensile strength.
Due to the reactivity of the aldehyde function, certain reactions will occur and precautions have to be undertaken:
The use of thiol-based scavengers should be avoided as their use can lead to thioacetal formation. Cysteines, homocysteines or other thiol bearing groups can form bicyclic analogous. N-Terminal allysine will react with amines, such as pyridines and form e.g. 1-piperidiene-6-carboxyl peptides. In case the N-terminal residue attached to the allysine is free, the product is likely be the corresponding peptide containing either 2-hydroxypiperidine carboxylic or 2-piperidien-6-carboxylic acid.
references
Hallberg; Vinyl Sulfide Cyclized Analogues of Angiotensin II with High Affinity and Full Agonist Activity at the AT1 Receptor. P. Johannesson, G. Lindeberg, A. Johansson, G. V.
Nikiforovich, A. Gogoll, B. Synnergren, M. Le Greves, F. Nyberg, A. Karlen, A.; J. Med. Chem. 2002; 45(9): 1767-1777.
Synthesis of allysine ethylene acetal using phenylalanine dehydrogenase from Thermoactinomyces intermedius; R.L. Hanson, J.M. Howell, T.L. LaPorte, M.J. Donovan, D.L. Cazzulino,
V. Zannella, M.A. Montana, V.B. Nanduri, S.R. Schwarz, R.F. Eiring, S.C. Durand, J.M. Wasylyk, W.L. Parker, M.S. Liu, F.J. Okuniewicz, B.-C. Chen, J.C. Harris, K.J. Natalie Jr, K.
Ramig, S. Swaminathan, V.W. Rosso, S.K. Pack, B.T. Lotz, P.J. Bernot, A. Rusowicz, D.A. Lust, K.S. Tse, J.J. Venit; Enzym. Microbial Techn. 2000;
26(5-6): 348-358. DOI: 10.1016/S0141-0229(99)00175-1.
Allysine peptides and derivatives; R.Dölz, E. Heidemann; Int. J. Peptide Protein Res. 1988; 32(4): 307-320. DOI: 10.1111/j.1399-3011.1988.tb01265.x.
Chemical synthesis of allysine ethylene acetal and conversion insitu into 1-piperideine-6-carboxylic acid: Key intermediate of the a-aminoadipic acid for ß-lactam antibiotics
biosynthesis; A. Rumbero, J.Fco. Martín, M.A. Lumbreras, P. Liras, C. Esmahan; Bioorganic & Medicinal Chemistry 1995; 3(9): 1237-1240.
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