Nα-Z-Nε-Boc-D-lysine
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Nα-Z-Nε-Boc-D-lysine

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Category
BOC-Amino Acids
Catalog number
BAT-004307
CAS number
66845-42-9
Molecular Formula
C19H28N2O6
Molecular Weight
380.40
Nα-Z-Nε-Boc-D-lysine
IUPAC Name
(2R)-6-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(phenylmethoxycarbonylamino)hexanoic acid
Synonyms
Z-D-Lys(Boc)-OH; N-Benzyloxycarbonyl-N'-(Tert-Butoxycarbonyl)-L-Lysine
Appearance
Colorless to light yellow oil
Purity
≥ 98% (HPLC)
Density
1.176±0.06 g/cm3(Predicted)
Melting Point
61-63°C
Boiling Point
587.0±50.0 °C(Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C19H28N2O6/c1-19(2,3)27-17(24)20-12-8-7-11-15(16(22)23)21-18(25)26-13-14-9-5-4-6-10-14/h4-6,9-10,15H,7-8,11-13H2,1-3H3,(H,20,24)(H,21,25)(H,22,23)/t15-/m1/s1
InChI Key
DYSBKEOCHROEGX-OAHLLOKOSA-N
Canonical SMILES
CC(C)(C)OC(=O)NCCCCC(C(=O)O)NC(=O)OCC1=CC=CC=C1
1.Synthesis of N-(1-deoxyhexitol-1-yl)amino acids, reference compounds for the nonenzymic glycosylation of proteins.
Walton DJ, Ison ER, Szarek WA. Carbohydr Res. 1984 May 15;128(1):37-49.
The N-(1-deoxy-D-mannitol-1-yl) and N-(1-deoxy-D-glucitol-1-yl) derivatives of L-valine, L-alanine, L-threonine, and L-leucine were prepared by reductive amination of D-mannose and D-glucose with the appropriate amino acids, in the presence of sodium cyanoborohydride. N epsilon-(1-Deoxy-D-mannitol-1-yl)- and N epsilon-(1-deoxy-D-glucitol-1-yl)-L-lysine were prepared by similar reactions of hexoses with N alpha-tert-butoxycarbonyl and N alpha-benzyloxycarbonyl-L-lysine, followed by removal of the protecting groups. The structures were confirmed by 1H-n.m.r. spectroscopy, which showed that each compound was completely free of its C-2 epimer. The synthetic compounds may be used as reference compounds for the identification of N-(1-deoxyhexitol-1-yl)amino acids formed when N-(1-deoxy-D-fructose-1-yl) groups of nonenzymically glycosylated proteins, of the hemoglobin A1c type, are reduced with sodium borohydride, and the protein is subjected to acid-catalyzed hydrolysis.
2.Enzymatic preparation of 5-hydroxy-L-proline, N-Cbz-5-hydroxy-L-proline, and N-Boc-5-hydroxy-L-proline from (α-N-protected)-L-ornithine using a transaminase or an amine oxidase.
Hanson RL1, Johnston RM, Goldberg SL, Parker WL, Patel RN. Enzyme Microb Technol. 2011 May 6;48(6-7):445-53. doi: 10.1016/j.enzmictec.2011.03.007. Epub 2011 Mar 26.
N-Cbz-4,5-dehydro-L-prolineamide or N-Boc-4,5-dehydro-L-prolineamide are alternative key intermediates for the synthesis of saxagliptin, a dipeptidyl peptidase IV (DPP4) inhibitor recently approved for treatment of type 2 diabetes mellitus. An efficient biocatalytic method was developed for conversion of L-ornithine, N-α-benzyloxycarbonyl (Cbz)-L-ornthine, and N-α-tert-butoxycarbonyl (Boc)-L-ornithine to 5-hydroxy-L-proline, N-Cbz-5-hydroxy-L-proline, and N-Boc-5-hydroxy-L-proline, respectively. Rec. Escherichia coli expressing lysine-ε-aminotransferase and rec Pichia pastoris expressing L-ornithine oxidase were used for these conversions. N-Cbz-5-hydroxy-L-proline, and N-Boc-5-hydroxy-L-proline were chemically converted to key intermediates N-Cbz-4,5-dehydro-L-prolineamide and N-Boc-4,5-dehydro-L-prolineamide, respectively.
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