Boc-Tyr(OtBu)-Aib-OH
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Boc-Tyr(OtBu)-Aib-OH

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Boc-Tyr(OtBu)-Aib-OH is a protected dipeptide used in peptide synthesis. The Boc (tert-Butoxycarbonyl) group protects the N-terminus of the tyrosine (Tyr) residue, preventing it from reacting during peptide assembly. The hydroxyl group on the tyrosine side chain is also protected by a tBu (tert-butyl) group, ensuring that it remains unreactive until the desired deprotection step. Aib (α-aminoisobutyric acid) is the second amino acid in the sequence, a non-natural amino acid known for inducing helical structures in peptides. The -OH at the C-terminus indicates a free carboxyl group, allowing for further peptide coupling. This compound is used to incorporate tyrosine and Aib into peptides, offering specific protective strategies for controlled synthesis and the introduction of conformational constraints.

Category
Peptide Synthesis Reagents
Catalog number
BAT-016536
CAS number
2639221-78-4
Molecular Formula
C22H34N2O6
Molecular Weight
422.52
Boc-Tyr(OtBu)-Aib-OH
IUPAC Name
2-methyl-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]propanoyl]amino]propanoic acid
Synonyms
Boc-Tyr(tBu)-Aib-OH; N-tert-Butoxycarbonyl-O4-tert-butyl-L-tyrosyl-alpha-methyl-alanine; (S)-2-(3-(4-(tert-Butoxy)phenyl)-2-((tert-butoxycarbonyl)amino)propanamido)-2-methylpropanoic acid
Appearance
White to off-white powder
Purity
≥95%
Density
1.129±0.06 g/cm3
Melting Point
152-156 °C
Boiling Point
629.1±55.0 °C at 760 mmHg
Sequence
Boc-Tyr(tBu)-Aib
Storage
Store at -20 °C
Solubility
Soluble in Chloroform (Very Slightly), Inglacial Acetic Acid (Sparingly), Methanol, N,N-Dimethylformamide, Water (Practically)
InChI
InChI=1S/C22H34N2O6/c1-20(2,3)29-15-11-9-14(10-12-15)13-16(23-19(28)30-21(4,5)6)17(25)24-22(7,8)18(26)27/h9-12,16H,13H2,1-8H3,(H,23,28)(H,24,25)(H,26,27)/t16-/m0/s1
InChI Key
NFZUXALUIGHTML-INIZCTEOSA-N
Canonical SMILES
CC(C)(C)OC1=CC=C(C=C1)CC(C(=O)NC(C)(C)C(=O)O)NC(=O)OC(C)(C)C
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