Name: Methyl (2R,4R)-1-Boc-4-hydroxypyrrolidine-2-carboxylate
Brand: BOC Sciences
Rating: 5 (1 reviews)

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Synonyms

(2R,4R)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate; Methyl cis-1-Boc-4-hydroxy-D-prolinate; 1-tert-butyl 2-methyl (2r,4r)-4-hydroxypyrrolidine-1,2-dicarboxylate

IUPAC Name

1-O-tert-butyl 2-O-methyl (2R,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-HTQZYQBOSA-N

Density

1.216±0.06 g/cm3

Melting Point

76°C

Boiling Point

335.2±42.0 °C at 760 mmHg

Methyl (2R,4R)-1-Boc-4-hydroxypyrrolidine-2-carboxylate, a chemical compound utilized in organic synthesis and pharmaceutical research, exhibits diverse applications.

Chiral Building Block: Serving as a pivotal chiral building block, this compound plays a crucial role in synthesizing intricate molecules, particularly in the pharmaceutical sector. Its specific stereochemistry facilitates the creation of enantiomerically pure substances, essential for designing drugs with targeted activity and minimal side effects. Such chiral building blocks are pivotal in crafting biologically active compounds with precision and efficacy.

Protecting Group Chemistry: The inclusion of the Boc (tert-butoxycarbonyl) group in this compound enables its utilization as a protecting group for amines during multi-step synthetic processes. Protecting groups are indispensable in organic synthesis for safeguarding reactive sites from engaging in undesirable reactions. Notably, the Boc group can be easily eliminated under mild acidic conditions, making it a practical choice for intricate synthetic sequences requiring meticulous protection and deprotection steps.

Research and Development: Widely employed in research environments, Methyl (2R,4R)-1-Boc-4-hydroxypyrrolidine-2-carboxylate facilitates the exploration of novel synthetic pathways and methodologies. Researchers leverage its distinct structure to delve into reaction mechanisms and pioneer innovative synthetic techniques. By broadening the toolkit accessible for chemical synthesis and material advancement, this compound aids in pushing the boundaries of research and development in diverse scientific fields.

Pharmacological Intermediate: Acting as a valuable intermediate in synthesizing pharmacologically active molecules, this compound plays a vital role in the creation of novel therapeutic compounds. Its integration into synthetic pathways empowers researchers to generate innovative molecules with potential therapeutic efficacy. By actively contributing to the realm of drug discovery and development, Methyl (2R,4R)-1-Boc-4-hydroxypyrrolidine-2-carboxylate propels efforts towards enhancing healthcare solutions and advancing pharmaceutical science.

1.Effect of methyl-beta-cyclodextrin on the viability and acrosome damage of sex-sorted sperm in frozen-thawed bovine semen.

Lee S1, Lee YS1, Lee SH2, Yang BK1, Park CK1. J Biol Res (Thessalon). 2016 Apr 12;23:5. doi: 10.1186/s40709-016-0043-x. eCollection 2016.

BACKGROUND: The regulation of methyl-beta-cyclodextrin (MBCD) on cryodamage on X- and Y-sperm during cryopreservation of semen was investigated. The semen was collected from ten healthy bulls of proven fertility by an artificial vagina. The bovine sperm treated with MBCD fresh solution (0, 1, 5, 10, and 20 mM). The sperms were evaluated for viability and acrosome damage using flow cytometry. Moreover, X- and Y-sperm in frozen-thawed bovine semen were sorted by flow cytometry after Hoechst 33342-dyed, and the viability and acrosome damage of sperms were analyzed.

2.Streptosporangium becharense sp. nov., an actinobacterium isolated from Saharan soil.

Chaabane Chaouch F1, Bouras N2, Mokrane S3, Zitouni A4, Schumann P5, Spröer C6, Sabaou N7, Klenk HP8. Int J Syst Evol Microbiol. 2016 Apr 13. doi: 10.1099/ijsem.0.001077. [Epub ahead of print]

The taxonomic position of a novel actinobacterium, strain SG1T, isolated from a Saharan soil sample collected from Béni-Abbès, Béchar (South-West Algeria) was established by using a polyphasic approach. The microorganism had morphological and chemical features that were consistent with its classification in the genus Streptosporangium. The cell-wall peptidoglycan contained meso-diaminopimelic acid. The whole-cell sugars contained ribose and glucose, but not madurose. The predominant menaquinones was MK-9(H2) and MK-9(H4). The polar lipid profile contained diphosphatidylglycerol, phosphatidylmethylethanolamine, phosphatidylethanolamine, phosphatidylhydroxymethylethanolamine, phosphatidylhydroxyethanolamine, phosphatidylglycerol, phosphatidylinositol and phosphatidylinositol mannosides. The predominant cellular fatty acids were C17 : 1 ω8c, iso-C16 : 0, 10-methyl C17 : 0, C18 : 1 ω9c and C17 : 0. 16S rRNA gene sequence similarity analysis supported the classification of the isolate in the genus Streptosporangium and indicated that it was most closely related to 'Streptosporangium subfuscum' DSM 46724T (99.

3.Metabolomics-guided analysis of isocoumarin production by Streptomyces species MBT76 and biotransformation of flavonoids and phenylpropanoids.

Wu C1, Zhu H2, van Wezel GP2, Choi YH3. Metabolomics. 2016;12:90. Epub 2016 Mar 30.

INTRODUCTION: Actinomycetes produce the majority of the antibiotics currently in clinical use. The efficiency of antibiotic production is affected by multiple factors such as nutrients, pH, temperature and growth phase. Finding the optimal harvesting time is crucial for successful isolation of the desired bioactive metabolites from actinomycetes, but for this conventional chemical analysis has limitations due to the metabolic complexity.

4.Induction of antigen-specific cytotoxic T-cell response by dendritic cells generated from ecto-mesenchymal stem cells infected with an adenovirus containing the MAGE-D4a gene.

Hu S1, Li B1, Shen X2, Zhang R3, Gao D1, Guo Q1, Jin Y4, Fei Z1. Oncol Lett. 2016 Apr;11(4):2886-2892. Epub 2016 Mar 7.

The present study aimed to investigate the feasibility of using ecto-mesenchymal stem cell (EMSC)-derived dendritic cells (DCs) for glioma immunotherapy following infection by a recombinant adenovirus containing the melanoma-associated antigen D4a (MAGE-D4a) gene. The ex vivo cultured EMSCs were infected by the adenoviral plasmid containing MAGE-D4a (pAd/MAGE-D4a). Efficiency of transfection was evaluated through the detection of green fluorescent protein-marked MAGE-D4a. The MAGE-EMSCs were induced to differentiate into DCs, termed as MAGE-EMSCs-DCs. The morphology was subsequently analyzed under a microscope, and methyl thiazolyl tetrazolium (MTT) and interferon-γ (IFN-γ) assays were performed to analyze the cytotoxicity of the MAGE-EMSC-DCs on the human glioma U251 cell line. Following purification by magnetic-activated cell sorting, the EMSCs grew into swirls, with a long spindle shape and were fibroblast-like. The gene transfected with recombinant adenovirus vectors maintained high and stable expression levels of MAGE-D4a, and its efficiency was increased in a multiplicity of infection-dependent manner.