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Application Area

Boc-D-Cys(Bzl)-ol

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category

Amino Alcohol

Catalog number

BAT-000604

CAS number

198470-16-5

Molecular Formula

C15H23NO3S

Molecular Weight

297.4

IUPAC Name

tert-butyl N-[(2S)-1-benzylsulfanyl-3-hydroxypropan-2-yl]carbamate

Synonyms

Boc-S-Benzyl-D-Cysteinol

Storage

Store at 2-8 °C

InChI

InChI=1S/C15H23NO3S/c1-15(2,3)19-14(18)16-13(9-17)11-20-10-12-7-5-4-6-8-12/h4-8,13,17H,9-11H2,1-3H3,(H,16,18)/t13-/m0/s1

InChI Key

MEZQRZMTIJTPIY-ZDUSSCGKSA-N

Canonical SMILES

CC(C)(C)OC(=O)NC(CO)CSCC1=CC=CC=C1

Boc-D-Cys(Bzl)-ol, a derivative of cysteine adorned with a protective Boc (tert-Butyloxycarbonyl) group and a benzyl group on the thiol, finds diverse applications in various fields. Here are four key applications:

Peptide Synthesis: Serving as a fundamental component in peptide synthesis, Boc-D-Cys(Bzl)-ol acts as a shielded building block that safeguards the amino group with the Boc group and the thiol with the benzyl group. This protective strategy prevents unintended reactions during peptide formation, ensuring the peptide’s structural stability and purity while enabling smooth assembly and purification processes.

Drug Development: In the intricate realm of medicinal chemistry, Boc-D-Cys(Bzl)-ol plays a pivotal role in crafting innovative therapeutic agents. By integrating this shielded amino acid into drug prototypes, researchers can explore its potential to foster disulfide bonds and construct robust cyclic structures. These alterations have the power to boost the biological efficacy, durability, and specificity of the resultant medications, pushing the boundaries of drug development.

Protein Engineering: Embracing the realm of protein engineering, Boc-D-Cys(Bzl)-ol emerges as a key player in introducing cysteine residues for precise modifications. The selective removal of protective groups under gentle conditions permits the controlled creation of disulfide bonds or the conjugation to other molecules. This meticulous technique empowers the generation of engineered proteins with enhanced functionalities or for intricate labeling studies, opening doors to refined protein manipulation.

Bioconjugation: A cornerstone in bioconjugation endeavors, Boc-D-Cys(Bzl)-ol acts as a linchpin for linking peptides and proteins to a myriad of molecules like fluorescent dyes or drug delivery systems. The shielded thiol group enables selective and efficient conjugation post-deprotection, granting meticulous oversight over the bioconjugation process. This application stands as a linchpin in the development of targeted therapeutics and diagnostic tools, steering the course of precision medicine.

2. Toluene and ethylbenzene aliphatic C-H bond oxidations initiated by a dicopper(II)-mu-1,2-peroxo complex

Heather R Lucas, Lei Li, Amy A Narducci Sarjeant, Michael A Vance, Edward I Solomon, Kenneth D Karlin J Am Chem Soc. 2009 Mar 11;131(9):3230-45. doi: 10.1021/ja807081d.

With an anisole-containing polypyridylamine potential tetradentate ligand (O)L, a mu-1,2-peroxo-dicopper(II) complex [{(O)LCu(II)}(2)(O(2)(2-))](2+) forms from the reaction of the mononuclear compound [Cu(I)((O)L)(MeCN)]B(C(6)F(5))(4) ((O)LCu(I)) with O(2) in noncoordinating solvents at -80 degrees C. Thermal decay of this peroxo complex in the presence of toluene or ethylbenzene leads to rarely seen C-H activation chemistry; benzaldehyde and acetophenone/1-phenylethanol mixtures, respectively, are formed. Experiments with (18)O(2) confirm that the oxygen source in the products is molecular O(2) and deuterium labeling experiments indicate k(H)/k(D) = 7.5 +/- 1 for the toluene oxygenation. The O(2)-reaction of [Cu(I)((Bz)L)(CH(3)CN)](+) ((Bz)LCu(I)) leads to a dicopper(III)-bis-mu-oxo species [{(Bz)LCu(III)}(2)(mu-O(2-))(2)](2+) at -80 degrees C, and from such solutions, very similar toluene oxygenation chemistry occurs. Ligand (Bz)L is a tridentate chelate, possessing the same moiety found in (O)L, but without the anisole O-atom donor. In these contexts, the nature of the oxidant species in or derived from [{(O)LCu(II)}(2)(O(2)(2-))](2+) is discussed and likely mechanisms of reaction initiated by toluene H-atom abstraction chemistry are detailed. To confirm the structural formulations of the dioxygen-adducts, UV-vis and resonance Raman spectroscopic studies have been carried out and these results are reported and compared to previously described systems including [{Cu(II)((Py)L)}(2)(O(2))](2+) ((Py)L = TMPA = tris(2-methylpyridyl)amine). Using (L)Cu(I), CO-binding properties (i.e., nu(C-O) values) along with electrochemical property comparisons, the relative donor abilities of (O)L, (Bz)L, and (Py)L are assessed.

3. A water-soluble, stable dipeptide NK1 receptor-selective neurokinin receptor antagonist with potent in vivo pharmacological effects: S18523

J Bonnet, N Kucharczyk, P Robineau, M Lonchampt, C Dacquet, D Regoli, J L Fauchère, E Canet Eur J Pharmacol. 1996 Aug 22;310(1):37-46. doi: 10.1016/0014-2999(96)00362-7.

The potassium salt of a chemically stabilized dipeptide, {1-[4-(1 H-tetrazol-5-yl)butyl]indol-3-yl}carbonyl-Hyp-Nal-N(methyl)-Bzl , (Hyp = (R)-4-hydroxy-L-proline; Nal = 3-L-(beta-naphthyl)-alanine), S18523, is described as a new water-soluble, potent and selective NK1 receptor antagonist. The low molecular weight antagonist (M(r) = 736) displays nanomolar potency (pA2 = 9.6) in the rabbit vena cava (NK1) bioassay and nanomolar affinity (pKi = 9.1) on the human NK1 receptor expressed by lymphoblastoma cells. It is devoid of mu-opiate affinity (Ki > 10(-4) M with respect to tritiated Tyr-DAla-Gly-MePhe-Gly-ol), has negligible calcium-channel affinity (estimated Ki = 2.6 x 10(-5) M, with respect to isradipine) and does not cause peritoneal mast-cell degranulation. S18523 has strong antinociceptive effects in three classical pain tests in vivo both by i.v. and p.o. routes. The dipeptide potently antagonizes bronchoconstriction provoked by exogenous substance P in the guinea-pig and acts longer than the non-peptide antagonist CP99994, when administered as aerosol. Finally, S18523 displays antiinflammatory properties, since it dose-dependently inhibits substance P-induced plasma extravasation both in the bladder (ID50 = 0.18 mg/kg i.v.) and bronchi (ID50 = 0.14 mg/kg i.v.) of the guinea-pig.