Boc-D-alanine
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Boc-D-alanine

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Category
BOC-Amino Acids
Catalog number
BAT-002702
CAS number
7764-95-6
Molecular Formula
C8H15NO4
Molecular Weight
189.20
Boc-D-alanine
IUPAC Name
(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
Synonyms
Boc-D-Ala-OH; N-(tert-Butoxycarbonyl)-D-alanine
Appearance
White to off-white powder
Purity
≥ 99% (HPLC)
Density
1.2321 g/cm3(rough estimate)
Melting Point
75-84 °C
Boiling Point
324.46°C (rough estimate)
Storage
Store at 2-8°C
InChI
InChI=1S/C8H15NO4/c1-5(6(10)11)9-7(12)13-8(2,3)4/h5H,1-4H3,(H,9,12)(H,10,11)/t5-/m1/s1
InChI Key
QVHJQCGUWFKTSE-RXMQYKEDSA-N
Canonical SMILES
CC(C(=O)O)NC(=O)OC(C)(C)C

Boc-D-alanine (N-tert-Butoxycarbonyl-D-alanine) is a protected amino acid derivative used primarily in peptide synthesis and various biochemical research. Here are some key applications of Boc-D-alanine:

Peptide Synthesis: Boc-D-alanine is commonly used in the synthesis of peptides and proteins due to its protective Boc group, which prevents unwanted reactions during peptide bond formation. The Boc group can be removed under mildly acidic conditions allowing for the incorporation of D-alanine into the peptide sequence. This application is essential in the development of synthetic peptides for research pharmaceuticals and biotechnology.

Drug Development: Boc-D-alanine plays a vital role in drug discovery and development, particularly in the design of peptidomimetics and enzyme inhibitors. Incorporating D-alanine into drug candidates can enhance their stability and resistance to enzymatic degradation. This leads to the development of more effective and long-lasting therapeutic agents.

Structural Biology: In structural studies, Boc-D-alanine is utilized to help elucidate protein folding and conformation. The incorporation of D-alanine can influence the secondary and tertiary structures of peptides providing insights into protein dynamics and stability. Researchers use these insights to better understand protein function and design novel biomolecules.

Bioconjugation: Boc-D-alanine serves as a building block in the development of bioconjugates where peptides are linked to other molecules like drugs fluorescent dyes or polymers. The presence of D-alanine can alter the properties of the resulting conjugate such as its biological activity binding affinity or stability. Bioconjugates have wide-ranging applications in areas such as targeted drug delivery diagnostics and imaging.

1. Noncovalent chiral functionalization of graphene with optically active helical polymers
Chonglei Ren, Yu Chen, Haiyang Zhang, Jianping Deng Macromol Rapid Commun. 2013 Sep;34(17):1368-74. doi: 10.1002/marc.201300342. Epub 2013 Jul 15.
Optically active helical substituted (co)polyacetylenes containing pendent pyrene groups are prepared and then noncovalently immobilized on graphene via π-π interactions. The resulting graphene composite is characterized by XRD, FTIR, Raman, circular dichroism, UV-vis absorption, TEM, TGA, and fluorescent spectroscopy techniques. The helical polyacetylene endows graphene with the desired optical activity. Also interestingly, the dispersibility of the functionalized graphene in tetrahydrofuran is remarkably improved due to the presence of the helical polymer chains. The present methodology opens new opportunities and serves as a versatile platform toward preparing novel graphene-based materials.
2. The first suspension polymerization for preparing optically active microparticles purely constructed from chirally helical substituted polyacetylenes
Haiyang Zhang, Jiexuan Song, Jianping Deng Macromol Rapid Commun. 2014 Jul;35(13):1216-23. doi: 10.1002/marc.201400067. Epub 2014 Apr 8.
Suspension polymerization has been extensively utilized with vinyl monomers to prepare vinyl-polymer microparticles (μm size; denoted MPs) with a variety of morphologies and significant applications. However, suspension polymerization of acetylenic monomers has remained a big challenge. This communication reports the first methodology for performing suspension polymerizations of acetylenic monomers, from which optically active microparticles (OAMPs) are constructed exclusively from helical substituted polyacetylenes. Chiral monomer (M1) and achiral monomer (M2) separately underwent suspension polymerization at room temperature in aqueous media in the presence of Rh-based catalyst with poly(vinyl alcohol) as a stabilizer, providing MPs (200~700 mm) in high yield (>80%). The obtained OAMPs, both crosslinked and non-crosslinked, were characterized by SEM, polarimetry, circular dichroism, and UV-vis spectroscopy. The chiral substituted polyacetylene chains constituting the MPs were found to adopt helices of predominantly one-handed screw sense, affording the particles with pronounced optical activity. The MPs derived from achiral M2 exhibited optical inactivity. The present study opens up new opportunities for preparing novel (non-)crosslinked microparticles derived from acetylenic monomers.
3. Magnetic Fe3O4-PS-polyacetylene composite microspheres showing chirality derived from helical substituted polyacetylene
Dong Liu, Ling Zhang, Mingkun Li, Wantai Yang, Jianping Deng Macromol Rapid Commun. 2012 Apr 23;33(8):672-7. doi: 10.1002/marc.201100776. Epub 2012 Feb 13.
This communication reports the first integration of two significant concepts, "macromolecular helicity-derived chirality," and "magneticity" in one single microsphere entity. The novel chiral magnetic composite microspheres consisted of magnetic Fe(3)O(4) nanoparticles and optically active helical substituted polyacetylene. Therefore, they exhibited both remarkable optical activity and magneticity. The microspheres adsorbed (R)-(+)-1-phenylethylamine much more quickly than the other enantiomer, demonstrating the potential applications of the chiral magnetic composite microspheres in chiral recognition and chiral resolution.
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