β-Cyclohexyl-D-alanine methyl ester hydrochloride
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β-Cyclohexyl-D-alanine methyl ester hydrochloride

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Category
D-Amino Acids
Catalog number
BAT-005818
CAS number
144644-00-8
Molecular Formula
C10H19NO2·HCl
Molecular Weight
221.70
β-Cyclohexyl-D-alanine methyl ester hydrochloride
IUPAC Name
methyl (2R)-2-amino-3-cyclohexylpropanoate;hydrochloride
Synonyms
D-Cha-OMe HCl; 3-Cyclohexyl-D-alanine methyl ester hydrochloride
Appearance
White powder
Purity
≥ 99% (Chiral purity)
Storage
Store at 2-8°C
InChI
InChI=1S/C10H19NO2.ClH/c1-13-10(12)9(11)7-8-5-3-2-4-6-8;/h8-9H,2-7,11H2,1H3;1H/t9-;/m1./s1
InChI Key
YLESODBCBYZUCT-SBSPUUFOSA-N
Canonical SMILES
COC(=O)C(CC1CCCCC1)N.Cl

β-Cyclohexyl-D-alanine methyl ester hydrochloride (BCHDAME-HCl) is a specialized chemical compound widely utilized in scientific research and pharmaceutical advancement. Here are the key applications of BCHDAME-HCl, presented with high perplexity and burstiness:

Peptide Synthesis: In the realm of peptide synthesis, BCHDAME-HCl emerges as a pivotal building block, shaping the conformation and biological activity of resultant peptides and peptidomimetics. Its integration into peptide chains offers avenues for designing peptide-based drugs with heightened stability and efficacy, showcasing its potential for innovation in drug development.

Enzyme Inhibition Studies: Delving into enzyme inhibition mechanisms, researchers harness BCHDAME-HCl as a versatile tool. It can mimic substrates or compete as an inhibitor, shedding light on enzyme active sites and catalytic pathways. These insightful investigations underpin the development of enzyme inhibitors as potent therapeutic modalities, emphasizing BCHDAME-HCl's role in advancing pharmaceutical research.

Pharmacokinetics Research: Within the realm of pharmacokinetics research, BCHDAME-HCl plays a pivotal role in deciphering the behaviors of alanine derivatives within biological systems. By unraveling its absorption, distribution, metabolism, and excretion patterns, scientists glean valuable insights into compound behavior in the body, elucidating pathways for optimizing drug design and delivery for improved therapeutic outcomes.

Chemical Synthesis: Unveiling its versatility in organic chemistry, BCHDAME-HCl serves as a key intermediate in synthesizing complex molecules. Exploiting its unique structural characteristics, researchers leverage BCHDAME-HCl to craft intricate chemical architectures, fostering the creation of novel materials and compounds with diverse industrial and pharmaceutical applications. This application underscores the instrumental role BCHDAME-HCl plays in driving innovation within chemical synthesis and material science realms.

1. Asymmetric Total Synthesis of Griseofamine B and Its Three Stereoisomers
Tao Sheng, Caiyun Ma, Guangyan Zhang, Xuan Pan, Zhanzhu Liu J Nat Prod. 2022 Apr 22;85(4):1128-1133. doi: 10.1021/acs.jnatprod.2c00069. Epub 2022 Mar 3.
The first total synthesis of griseofamine B is described starting from l-4-bromo tryptophan methyl ester hydrochloride via five steps and in 18% overall yield. Its three stereoisomers were also synthesized following the same procedure with the yields of 5%, 19%, and 5%, respectively. In vitro antibacterial activities were also evaluated. All four compounds exhibited less potent activity than griseofamine A.
2. l-Alanine methyl ester hydro-chloride monohydrate
Martin Lutz, Arie Schouten Acta Crystallogr Sect E Struct Rep Online. 2011 Feb 9;67(Pt 3):o586. doi: 10.1107/S160053681100420X.
The enanti-opure title compound, C(4)H(10)NO(2) (+)·Cl(-)·H(2)O, forms a two-dimensional network by inter-molecular hydrogen bonding parallel to (010). Non-merohedral twinning with a twofold rotation about the reciprocal c* axis as twin operation was taken into account during intensity integration and structure refinement. This twinning leads to alternative orientations of the stacked hydrogen-bonded layers.
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