Name: Boc-L-4-trans-hydroxyproline methyl ester
Brand: BOC Sciences
Rating: 5 (1 reviews)

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Synonyms

Boc-L-Hyp-OMe; 1-tert-Butyl-2-methyl; (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate; Boc L Hyp OMe

IUPAC Name

1-O-tert-butyl 2-O-methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate

Canonical SMILES

CC(C)(C)OC(=O)N1CC(CC1C(=O)OC)O

InChI

InChI=1S/C11H19NO5/c1-11(2,3)17-10(15)12-6-7(13)5-8(12)9(14)16-4/h7-8,13H,5-6H2,1-4H3/t7-,8+/m1/s1

InChIKey

MZMNEDXVUJLQAF-SFYZADRCSA-N

Density

1.2±0.1 g/cm3

Melting Point

96 °C

Appearance

White Powder

Storage

Store at 2-8 °C

Boiling Point

335.2±42.0 °C at 760 mmHg

Boc-L-4-trans-hydroxyproline methyl ester, a protected derivative of 4-trans-hydroxyproline, plays a pivotal role in bioscience and chemical research. Here are four key applications:

Peptide Synthesis: Widely employed in peptide and protein synthesis, Boc-L-4-trans-hydroxyproline methyl ester is instrumental in exploring the function of hydroxyproline in collagen stability and activity. Researchers utilize this ester to construct peptides that replicate natural proteins, facilitating in-depth structural and functional assessments.

Drug Development: In the realm of medicinal chemistry, this compound holds significant value for crafting proline-rich peptides and small molecules with potential therapeutic applications. These peptides serve as promising drug candidates for conditions like fibrosis and cancer. The utilization of Boc-protected hydroxyproline allows for meticulous refinement and enhancement of drug characteristics.

Structural Biology: Within structural biology, Boc-L-4-trans-hydroxyproline methyl ester is a critical tool for probing protein folding and stability. The presence of hydroxyproline residues influences the three-dimensional structures of proteins, such as collagen. Incorporating this ester into protein constructs enables scientists to analyze its impact on protein structure and stability using advanced techniques like X-ray crystallography and NMR spectroscopy.

Biotechnology: In the field of biotechnology, Boc-L-4-trans-hydroxyproline methyl ester is harnessed to engineer modified enzymes and proteins with superior properties. By integrating hydroxyproline into protein sequences, researchers can enhance thermal stability, proteolysis resistance, and overall protein functionality. This capability proves invaluable in industrial settings where robust and enduring proteins are essential for various applications.

1. Alginate ester: New moisture-scavenging excipients for direct compressible pharmaceutical tableting

Noelia M Sanchez-Ballester, Philippe Trens, Jean-Christophe Rossi, Ian Soulairol Carbohydr Polym. 2022 Dec 1;297:120063. doi: 10.1016/j.carbpol.2022.120063. Epub 2022 Aug 31.

The objective of this work is to evaluate methyl ester alginates and alginic acid (AA) as moisture-scavenging excipients for the formulation of aspirin tablets obtained by direct compression. The tablets were stored at accelerated conditions (40 °C/75 % RH) and assessed for changes in tensile strength, mass, thickness and disintegration time. While moisture caused a reduction in the hardness of MCC and AA tablets, hardness of the tablets made from methylated materials was virtually unaffected. The physical stability of alginate ester tablets was found to be related to their increased plastic deformation leading to extended interparticle contact with less impact on tablet porosity. Finally, the combination of higher moisture affinity and lower water dissociation exhibited by alginates esters resulted in tablets with the lowest aspirin degradation. These findings suggest that excipients with high water retention can act as moisture-scavengers without losing their functional properties and reducing the degradation of moisture-sensitive drugs.

2. O-Methylation of carboxylic acids with streptozotocin

Li-Yan Zeng, Yang Liu, Jiakun Han, Jinhong Chen, Shuwen Liu, Baomin Xi Org Biomol Chem. 2022 Jul 6;20(26):5230-5233. doi: 10.1039/d2ob00578f.

The clinically used DNA-alkylating drug streptozotocin (STZ) was investigated using a simple work-up as an O-methylating agent to transform various carboxylic acids, sulfonic acids and phosphorous acids into corresponding methyl esters, and did so with yields of up to 97% in 4 h at room temperature. Good substrate tolerance was observed, and benefited from the mild conditions and compatibility of the reaction with water.

3. Acridinium Ester Chemiluminescence: Methyl Substitution on the Acridine Moiety

Manabu Nakazono, Shinkoh Nanbu, Takeyuki Akita, Kenji Hamase J Oleo Sci. 2021;70(11):1677-1684. doi: 10.5650/jos.ess21186.

Methyl groups were introduced on the acridine moiety in chemiluminescent acridinium esters that have electron-withdrawing groups (trifluoromethyl, cyano, nitro, ethoxycarbonyl) at the 4-position on the phenyl ester. The introduction of methyl groups at the 2-, 2,7-, and 2,3,6,7-positions on the acridine moiety shifted the optimal pH that gave relatively strong chemiluminescence intensity from neutral conditions to alkaline conditions. 4-(Ethoxycarbonyl)phenyl 2,3,6,7,10-pentamethyl-10λ4-acridine-9-carboxylate, trifluoromethanesulfonate salt showed long-lasting chemiluminescence under alkaline conditions. Acridinium esters to determine hydrogen peroxide concentration at pH 7-10 were newly developed.