Boc-(4R)-4-azido-D-proline - CAS 650601-59-5

Boc-(4R)-4-azido-D-proline - CAS 650601-59-5 Catalog number: BADC-01993

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Category
ADCs Linker
Product Name
Boc-(4R)-4-azido-D-proline
CAS
650601-59-5
Catalog Number
BADC-01993
Molecular Formula
C10H16N4O4
Molecular Weight
256.30

Ordering Information

Catalog Number Size Price Quantity
BADC-01993 -- $--
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Synonyms
Boc-D-Pro(4-N3) (2R,4R); Boc-(2R,4R)-4-azidoproline; (2R,4R)-4-Azido-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester
IUPAC Name
(2R,4R)-4-azido-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
Canonical SMILES
CC(C)(C)OC(=O)N1CC(CC1C(=O)O)N=[N+]=[N-]
InChI
InChI=1S/C10H16N4O4/c1-10(2,3)18-9(17)14-5-6(12-13-11)4-7(14)8(15)16/h6-7H,4-5H2,1-3H3,(H,15,16)/t6-,7-/m1/s1
InChIKey
JZEOWBJXFSZTJU-RNFRBKRXSA-N
Melting Point
76-80°C
Appearance
White crystalline powder
Purity
≥ 99% (Assay by titration, HPLC)
Storage
Store at 2-8 °C

Boc-(4R)-4-azido-D-proline is a versatile compound used in various chemical and biological research applications. Here are some key applications of Boc-(4R)-4-azido-D-proline:

Peptide Synthesis: Boc-(4R)-4-azido-D-proline is used as a building block in the synthesis of peptides. Its azido group allows for the introduction of additional functional groups via click chemistry, facilitating the modification of peptides post-synthesis. This aids in creating complex peptide constructs for use in drug development and biochemical studies.

Chemical Biology: This compound serves as an important tool in chemical biology for studying protein structures and interactions. The azido group can be selectively reacted with alkynes through copper-catalyzed azide-alkyne cycloaddition (CuAAC), allowing researchers to label proteins with probes. This is invaluable for imaging and tracking proteins within cells.

Protein Engineering: In protein engineering, Boc-(4R)-4-azido-D-proline is incorporated into proteins to introduce site-specific modifications. The azide moiety can be used for bioconjugation with other molecules, such as dyes and therapeutic agents. This approach is crucial for developing novel protein-based therapeutics and diagnostics.

Bioorthogonal Chemistry: Boc-(4R)-4-azido-D-proline is utilized in bioorthogonal reactions, which occur without interfering with native biochemical processes. Its use in bioorthogonal chemistry enables precise modifications in living cells, facilitating studies on cellular functions and dynamics. This technique is particularly useful for in vivo studies and therapeutic interventions.

1. Synthesis of methyl N-Boc-(2S,4R)-4-methylpipecolate
Kuo-Yuan Hung, Paul W R Harris, Margaret A Brimble J Org Chem. 2010 Dec 17;75(24):8728-31. doi: 10.1021/jo102038q. Epub 2010 Nov 23.
An efficient stereoselective synthesis of fully protected (2S,4R)-4-methylpipecolic acid has been developed. The synthesis was achieved by initial asymmetric α-alkylation of glycine with a chiral iodide, affording the linear precursor as a single stereoisomer. Subsequent aldehyde formation using OsO(4)/NaIO(4) followed by immediate intramolecular cyclization afforded an enamine that was then subjected to hydrogenation to give the final compound in 23% yield over 10 steps.
2. Crystal Structure Analysis of 4-Oxo, 4-hydroxy- and 4-alkyl-7-bromopyrazolo[5,1- c][1,2,4]triazines
Sergey M Ivanov, Denis S Koltun J Chem Crystallogr. 2022 Dec 17;1-12. doi: 10.1007/s10870-022-00973-x. Online ahead of print.
The crystal structures of 8-R1-7-bromo-3-tert-butyl-1-R2-pyrazolo[5,1-c][1,2,4]triazin-4(1H)-ones 1a-c, 2a,c (R1 = CN, CO2Et, NO2, R2 = H, 1:1 and 3:1 solvates with DMSO; R1 = CN, CO2Et, R2 = CH2Boc), 8-R1-7-bromo-3-tert-butyl-1-R2-1,4-dihydropyrazolo[5,1-c][1,2,4]triazin-4-ols 3a,b (R1 = CN, R2 = n-Bu; R1 = Br, R2 = CH2Boc), 1,4-dihydro- and aromatic 7-R3-3-tert-butyl-4-R4-8-methylpyrazolo[5,1-c][1,2,4]triazines 5a,b, 6 (R3 = H, R4 = n-Pr; R3 = Br, R4 = n-Bu) were investigated by X-ray diffraction analysis. The structural preferences and different packing modes based on the intermolecular interactions were analyzed by the Hirshfeld surface and energy framework analysis. Graphical abstract: The crystal structures of ten 3-tert-butyl-4-oxo, 4-hydroxy- and 4-alkyl-7-bromopyrazolo[5,1-c][1,2,4]triazines including non-solvated, 1:1 and 3:1 solvates with DMSO were investigated by single crystal X-ray diffraction, Hirshfeld surface and energy framework analyses. Supplementary information: The online version contains supplementary material available at 10.1007/s10870-022-00973-x.
3. Proline C-H Bonds as Loci for Proline Assembly via C-H/O Interactions
Noah J Daniecki, Megh R Bhatt, Glenn P A Yap, Neal J Zondlo Chembiochem. 2022 Dec 16;23(24):e202200409. doi: 10.1002/cbic.202200409. Epub 2022 Nov 24.
Proline residues within proteins lack a traditional hydrogen bond donor. However, the hydrogens of the proline ring are all sterically accessible, with polarized C-H bonds at Hα and Hδ that exhibit greater partial positive character and can be utilized as alternative sites for molecular recognition. C-H/O interactions, between proline C-H bonds and oxygen lone pairs, have been previously identified as modes of recognition within protein structures and for higher-order assembly of protein structures. In order to better understand intermolecular recognition of proline residues, a series of proline derivatives was synthesized, including 4R-hydroxyproline nitrobenzoate methyl ester, acylated on the proline nitrogen with bromoacetyl and glycolyl groups, and Boc-4S-(4-iodophenyl)hydroxyproline methyl amide. All three derivatives exhibited multiple close intermolecular C-H/O interactions in the crystallographic state, with H⋅⋅⋅O distances as close as 2.3 Å. These observed distances are well below the 2.72 Å sum of the van der Waals radii of H and O, and suggest that these interactions are particularly favorable. In order to generalize these results, we further analyzed the role of C-H/O interactions in all previously crystallized derivatives of these amino acids, and found that all 26 structures exhibited close intermolecular C-H/O interactions. Finally, we analyzed all proline residues in the Cambridge Structural Database of small-molecule crystal structures. We found that the majority of these structures exhibited intermolecular C-H/O interactions at proline C-H bonds, suggesting that C-H/O interactions are an inherent and important mode for recognition of and higher-order assembly at proline residues. Due to steric accessibility and multiple polarized C-H bonds, proline residues are uniquely positioned as sites for binding and recognition via C-H/O interactions.
The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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