Boc-O-benzyl-D-tyrosine
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Boc-O-benzyl-D-tyrosine

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Category
BOC-Amino Acids
Catalog number
BAT-002859
CAS number
63769-58-4
Molecular Formula
C21H25NO5
Molecular Weight
371.40
Boc-O-benzyl-D-tyrosine
IUPAC Name
(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(4-phenylmethoxyphenyl)propanoic acid
Synonyms
Boc-D-Tyr(Bzl)-OH
Appearance
White to off-white powder
Purity
≥ 98% (HPLC)
Density
1.185±0.06 g/cm3(Predicted)
Melting Point
108-113 °C
Boiling Point
552.4±50.0 °C(Predicted)
Storage
Store at 2-8°C
InChI
InChI=1S/C21H25NO5/c1-21(2,3)27-20(25)22-18(19(23)24)13-15-9-11-17(12-10-15)26-14-16-7-5-4-6-8-16/h4-12,18H,13-14H2,1-3H3,(H,22,25)(H,23,24)/t18-/m1/s1
InChI Key
ZAVSPTOJKOFMTA-GOSISDBHSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC1=CC=C(C=C1)OCC2=CC=CC=C2)C(=O)O
1.Solid-phase synthesis of peptides via alpha, beta-unsaturated amino acids: oxytocin, simultaneous incorporation of amide functions in COOH-terminal and endo-positions.
Noda K, Gazis D, Gross E. Int J Pept Protein Res. 1982 Apr;19(4):413-9.
Oxytocin was synthesized via the solid-phase method using dehydroalanine as pseudo-protecting group of the carboxyl-terminal as well as the omega-amide functions of asparagine and glutamine in endo-position. Starting with Boc-Gly-Dha-resin and using Boc-L-Asp(Dha-NHEt)-OH and Boc-L-Glu(Dha-NHEt)-OH as precursors of asparagine and glutamine, respectively, oxytocin was assembled in stepwise manner under solid phase synthesis conditions. Treatment of the protected [Glu(Dha-NHEt)4, Asp(Dha-NHEt)5]-oxytocin-Dha-resin with 1 n HCl in glacial acetic acid in the presence of 3 equiv. water removed the peptide from the support with the simultaneous formation of the asparagine and glutamine residues to give the protected nonapeptide amide: Cbz-Cys(Bzl)-Tyr(Bzl)-Ile-Gln-Asn-Cys(Bzl)-Pro-Leu-Gly-NH2, which was deprotected with sodium in liquid ammonia and then oxidized with diiodoethane to give oxytocin. After purification by gel chromatography and countercurrent distribution, the product displayed the chemical and physical properties and oxytocic activity (533 +/- 301U/mg) of a standard oxytocin preparation.
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