Boc-L-isoleucine
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Boc-L-isoleucine

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Category
BOC-Amino Acids
Catalog number
BAT-002784
CAS number
13139-16-7
Molecular Formula
C11H21NO4
Molecular Weight
231.30
Boc-L-isoleucine
IUPAC Name
(2S,3S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid
Synonyms
Boc-L-Ile-OH; Boc-(2S,3S)-2-amino-3-methylpentanoic acid; N-(tert-Butoxycarbonyl)-L-isoleucine
Appearance
White crystalline powder
Purity
≥ 99% (Assay)
Density
1.1202 g/cm3(rough estimate)
Melting Point
69-73 °C
Boiling Point
373.37°C (rough estimate)
Storage
Store at 2-8 °C
InChI
InChI=1S/C11H21NO4/c1-6-7(2)8(9(13)14)12-10(15)16-11(3,4)5/h7-8H,6H2,1-5H3,(H,12,15)(H,13,14)/t7-,8-/m0/s1
InChI Key
QJCNLJWUIOIMMF-YUMQZZPRSA-N
Canonical SMILES
CCC(C)C(C(=O)O)NC(=O)OC(C)(C)C
1.Controlled synthesis of amino acid-based pH-responsive chiral polymers and self-assembly of their block copolymers.
Bauri K1, Roy SG, Pant S, De P. Langmuir. 2013 Feb 26;29(8):2764-74. doi: 10.1021/la304918s. Epub 2013 Feb 11.
Leucine/isoleucine side chain polymers are of interest due to their hydrophobicity and reported role in the formation of α-helical structures. The synthesis and reversible addition-fragmentation chain transfer (RAFT) polymerization of amino acid-based chiral monomers, namely Boc-L-leucine methacryloyloxyethyl ester (Boc-L-Leu-HEMA, 1a), Boc-L-leucine acryloyloxyethyl ester (Boc-L-Leu-HEA, 1b), Boc-L-isoleucine methacryloyloxyethyl ester (Boc-L-Ile-HEMA, 1c), and Boc-L-isoleucine acryloyloxyethyl ester (Boc-L-Ile-HEA, 1d), are reported. The controlled nature of the polymerization of the said chiral monomers in N, N-dimethylformamide (DMF) at 70 °C is evident from the formation of narrow polydisperse polymers, the molecular weight controlled by the monomer/chain transfer agent (CTA) molar ratio and the linear relationship between molecular weight and monomer conversion. The resulting well-defined polymers were used as macro-CTAs to prepare corresponding diblock copolymers by RAFT polymerization of methyl (meth)acrylate monomers.
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