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

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Synonyms

Boc-cis-L-Hyp-OMe; Boc cis L Hyp OMe

IUPAC Name

1-O-tert-butyl 2-O-methyl (2S,4S)-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-/m0/s1

InChIKey

MZMNEDXVUJLQAF-YUMQZZPRSA-N

Density

1.216 g/cm3

Melting Point

79-84 °C

Appearance

White solid

Storage

Store at 2-8 °C

Boiling Point

335.244°C at 760 mmHg

Boc-cis-L-4-hydroxyproline methyl ester, a specialized amino acid derivative, finds its application in diverse biochemical and pharmaceutical realms. Here are the key applications of this compound, presented with a high degree of perplexity and burstiness:

Peptide Synthesis: Integral to the synthesis of intricate peptides and proteins, Boc-cis-L-4-hydroxyproline methyl ester acts as a fundamental component in solid-phase peptide synthesis. Its role in incorporating hydroxyproline residues into peptide chains is pivotal for constructing peptides with specific structures and biological functions, particularly those that emulate the complexity of collagen.

Pharmaceutical Development: With a focus on proline-rich drugs and biomolecules, this compound plays an essential role in enhancing the stability, activity, and bioavailability of peptide-based therapeutics. Scientists leverage the unique structure of Boc-cis-L-4-hydroxyproline methyl ester to design and synthesize novel drug candidates for combating various diseases, including cancer and fibrosis, opening new avenues in pharmaceutical innovation.

Structural Biology: In the realm of structural biology, researchers utilize Boc-cis-L-4-hydroxyproline methyl ester to explore protein folding and stability mechanisms. By integrating hydroxyproline into synthetic peptides and proteins, scientists delve into the significance of this amino acid in preserving collagen structure and other protein conformations, offering insights into protein misfolding disorders and guiding the development of therapeutic interventions.

Biomaterials Research: Within the domain of biomaterials research, Boc-cis-L-4-hydroxyproline methyl ester serves as a key component in fabricating hydroxyproline-containing polymers and hydrogels. These materials mimic the extracellular matrix, supporting applications in tissue engineering and regenerative medicine. By enhancing the mechanical properties and biocompatibility of biomaterials, researchers craft advanced scaffolds for tissue repair and regeneration, pushing the boundaries of regenerative medicine forward.

1.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.

2.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.

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.Preparation of Methylated Products of A-type Procyanidin Trimers in Cinnamon Bark and Their Protective Effects on Pancreatic β-Cell.

Chen L1, Chen L1, Wang T2, Yuan P1, Chen K1,2, Jia Q1, Wang H2, Li Y1. J Food Sci. 2016 Apr 13. doi: 10.1111/1750-3841.13294. [Epub ahead of print]

Polyphenols are partial metabolized to methylated conjugations in vivo, and then could modify bioavailability and bioactivity related to the uptake of parent compounds. Our previous studies have found that the antidiabetic effects of cinnamon barks are mainly related to polyphenol components, particularly A-type procyanidin trimer cinnamtannin-1 (CT1). It is necessary to understand the antidiabetic activity of methylations of CT1, nevertheless, sufficient amounts of methylated CT1 are difficult to obtain from metabolites in vivo. In this study, O-methyl derivatives of CT1 were prepared through one-pot methyl iodide reaction and isolation via column chromatography and RP-HPLC semipreparation. The structures of O-methyl substituents were determined through NMR (Nuclear Magnetic Resonance) and HPLC-ESI-MS (High-performance liquid chromatography-electrospray ionization-mass spectrometry). Five purified O-methyl substituents and 2 isomers of CT1 were obtained.