Boc-3-(1-naphthyl)-L-alanine
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Boc-3-(1-naphthyl)-L-alanine

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Boc-3-(1-naphthyl)-L-alanine, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

Category
BOC-Amino Acids
Catalog number
BAT-007956
CAS number
55447-00-2
Molecular Formula
C18H21NO4
Molecular Weight
315.36
Boc-3-(1-naphthyl)-L-alanine
IUPAC Name
(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-naphthalen-1-ylpropanoic acid
Synonyms
Boc-L-Ala(1-naphthyl)-OH; Boc-(S)-2-amino-3-(naphthalen-1-yl)propanoic acid; Boc-3-(1-naphthyl)-L-alanine; Boc-L-1-naphthylalanine; Boc-1-Nal-OH; (S)-N-Boc-L-(1-naphthyl)alanine; (2S)-2-[(tert-butoxy)carbonylamino]-3-naphthylpropanoic acid; Boc-L-3-(1-Naphthyl)-alanine; Boc L Nal OH
Appearance
White to off-white powder
Purity
≥ 99% (HPLC)
Density
1.200 g/cm3
Melting Point
144 °C
Boiling Point
512.2 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C18H21NO4/c1-18(2,3)23-17(22)19-15(16(20)21)11-13-9-6-8-12-7-4-5-10-14(12)13/h4-10,15H,11H2,1-3H3,(H,19,22)(H,20,21)/t15-/m0/s1
InChI Key
KHHIGWRTNILXLL-HNNXBMFYSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC1=CC=CC2=CC=CC=C21)C(=O)O

Boc-3-(1-naphthyl)-L-alanine, a versatile chemical building block, finds widespread use in synthetic chemistry and pharmaceutical research. Here are the key applications of Boc-3-(1-naphthyl)-L-alanine presented with high perplexity and burstiness:

Peptide Synthesis: Renowned for its role in peptide synthesis, Boc-3-(1-naphthyl)-L-alanine is an essential component due to its protected amino group. During the intricate process of peptide assembly, it serves to shield the amine functionality safeguarding against undesired reactions. This safeguard ensures the precise formation of peptide bonds culminating in the creation of high-purity peptide chains with exceptional fidelity.

Drug Development: Positioned at the forefront of drug innovation, Boc-3-(1-naphthyl)-L-alanine emerges as a pivotal precursor in the quest for novel therapeutic agents. Its unique molecular structure renders it a valuable asset in the formulation of enzyme inhibitors and receptor modulators. Through the strategic integration of this compound researchers can explore uncharted territories of drug development unveiling promising candidates with enhanced efficacy and unparalleled selectivity.

Enzyme Inhibition Studies: Serving as a cornerstone in enzyme inhibition studies, Boc-3-(1-naphthyl)-L-alanine plays a pivotal role in unraveling the intricate complexities of enzyme-substrate interactions. Researchers leverage its properties to delve into the binding affinities and catalytic activities of proteolytic enzymes particularly proteases. This investigative tool aids in deciphering enzyme mechanisms and pinpointing potent inhibitors with far-reaching implications for therapeutic interventions.

Structural Biology: At the intersection of structural biology, Boc-3-(1-naphthyl)-L-alanine emerges as a key player in deciphering the conformational properties of amino acids and peptides. Through its incorporation into model systems scientists embark on a journey to unravel its impact on secondary and tertiary structures. This knowledge is indispensable for unraveling the enigmatic realms of protein folding and stability bearing profound implications for drug design and the burgeoning field of biotechnology.

1.Synthesis of N-Boc-Propargylic and Allylic Amines by Reaction of Organomagnesium Reagents with N-Boc-Aminals and Their Oxidation to N-Boc-Ketimines.
Kano T1, Kobayashi R1, Maruoka K1. Org Lett. 2016 Jan 15;18(2):276-9. doi: 10.1021/acs.orglett.5b03446. Epub 2016 Jan 4.
Previously inaccessible N-Boc-protected propargylic and allylic amines were synthesized by the reaction between N-Boc-aminals and organomagnesium reagents through the in situ generated N-Boc-imine intermediates. The obtained N-Boc-propargylic amines could be readily converted into unprecedented N-Boc-ketimines by oxidation with manganese dioxide.
2.Copper-catalyzed borylative coupling of vinylazaarenes and N-Boc imines.
Smith JJ1, Best D1, Lam HW1. Chem Commun (Camb). 2016 Feb 25;52(19):3770-2. doi: 10.1039/c6cc00603e.
Cu-catalyzed three-component couplings of vinylazaarenes, B2(pin)2, and N-Boc imines are described. Oxidation of the initially formed boronate gives azaarene-containing, Boc-protected amino alcohols with reasonable to good diastereoselectivities.
3.Direct Amidation of N-Boc- and N-Cbz-Protected Amines via Rhodium-Catalyzed Coupling of Arylboroxines and Carbamates.
Lim DS1, Lew TT1, Zhang Y1. Org Lett. 2015 Dec 18;17(24):6054-7. doi: 10.1021/acs.orglett.5b03061. Epub 2015 Nov 25.
N-Boc- and N-Cbz-protected amines are directly converted into amides by a novel rhodium-catalyzed coupling of arylboroxines and carbamates, replacing the traditional two-step deprotection-condensation sequence. Both protected anilines and aliphatic amines are efficiently transformed into a wide variety of secondary benzamides, including sterically hindered and electron-deficient amides, as well as in the presence of acid-labile and reducible functional groups.
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