21947-98-8

Basic information

• Product Name: N-Boc-S-Trityl-L-cysteine
• Synonyms: Nα-Boc-S-trityl-L-cysteine, N-(tert-Butoxycarbonyl)-S-trityl-L-cysteine;Boc-S-Trityl-Cys-OH;N-(tert-Butyloxycarbonyl)-S-trityl-L-cysteine;N-[(1,1-Dimethylethoxy)carbonyl]-S-(triphenylmethyl)-L-cysteine;N-Boc-S-Trityl-L-Cys-OH;BOC-S-trityl-L-cysteine,99%;2-(tert-butoxycarbonylamino)-3-[tri(phenyl)methylthio]propionic acid;2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[tri(phenyl)methylsulfanyl]propanoic acid
• CAS NO: 21947-98-8
• Molecular Formula: C₂₇H₂₉NO₄S
• Molecular Weight: 463.59
• EINECS: 244-674-6
• Product Categories: Cysteine [Cys, C];Boc-Amino Acids and Derivative;Boc-Amino acid series;Amino Acid Derivatives;Amino Acids
• Mol File: 21947-98-8.mol

Chemical Properties

• Melting Point: 143-146 °C(lit.)
• Boiling Point: 610.9 °C at 760 mmHg
• Flash Point: 323.3 °C
• Appearance: White to yellow crystalline powder
• Density: 1.2 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.596
• Storage Temp.: 2-8°C
• PKA: 3.82±0.10(Predicted)
• BRN: 2028965
• CAS DataBase Reference: N-Boc-S-Trityl-L-cysteine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-S-Trityl-L-cysteine(21947-98-8)
• EPA Substance Registry System: N-Boc-S-Trityl-L-cysteine(21947-98-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 21947-98-8(Hazardous Substances Data)

Usage

Chemical Properties

White to yellow crystalline powder

InChI:InChI=1/C27H29NO4S/c1-26(2,3)32-25(31)28-23(24(29)30)19-33-27(20-13-7-4-8-14-20,21-15-9-5-10-16-21)22-17-11-6-12-18-22/h4-18,23H,19H2,1-3H3,(H,28,31)(H,29,30)/t23-/m1/s1

Upstream product

• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 2799-07-7 S-trityl-L-cysteine 
• 76-84-6 triphenylmethyl alcohol 
• 52-90-4 L-Cysteine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 76-83-5 trityl chloride 
• 109-89-7 diethylamine 
• 103213-32-7 N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 52-89-1 l-cysteine hydrochloride 

Downstream Products

• 205044-74-2 {(R)-2-[4-(3-Bromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl)-piperazin-1-yl]-2-oxo-1-tritylsulfanylmethyl-ethyl}-carbamic acid tert-butyl ester 
• 205044-28-6 [(R)-2-(4-{2-[4-(3-Bromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl)-piperazin-1-yl]-2-oxo-ethyl}-piperidin-1-yl)-2-oxo-1-tritylsulfanylmethyl-ethyl]-carbamic acid tert-butyl ester 
• 256368-78-2 2-(2-{[1-(2-tert-butoxycarbonylamino-3-tritylsulfanyl-propionyl)-4-phenyl-piperidine-4-carbonyl]-amino}-4-methyl-pentanoylamino)-propionic acid tert-butyl ester 
• 566916-29-8 Boc-Cys(Trt)-PNB 
• 158009-01-9 tert-Butyl N^α-tert-butoxycarbonyl-L-(S-trityl)cysteinate hydrochloride 
• 851048-01-6 Acetic acid (2S,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-[4-((R)-2-tert-butoxycarbonylamino-3-tritylsulfanyl-propionylamino)-butyrylamino]-tetrahydro-pyran-4-yl ester 
• 922139-32-0 [1-(3-{4-[(4-acetylamino-1-methyl-1H-pyrrole-2-carbonyl)-amino]-2-[5-(3-dimethylamino-propylcarbamoyl)-1-methyl-1H-pyrrol-3-ylcarbamoyl]-pyrrol-1-yl}-propylcarbamoyl)-2-tritylsulfanyl-ethyl]-carbamic acid tert-butyl ester 
• 40472-53-5 BOCCys(Trit)ProOH 
• 406728-64-1 {1-[2-(3,4-dihydroxyphenyl)ethyl]carbamoyl-2-(tritylsulfanyl)ethyl}carbamic acid tert-butyl ester 

Relevant articles and documents

CGG repeat DNA assisted dimerization of CGG/CGG binding molecule through intermolecular disulfide formation

A new DNA binding small molecule, NCD-CC is reported. NCD-CC has a NCD domain, which recognizes the G-G mismatch in a CGG/CGG triad, and a cysteinylcystein (CC) moiety. Dimerization of NCD-CC through intermolecular disulfide bond formation was accelerated in the presence of CGG repeat DNA.

Polycysteine as a new type of radio-protector ameliorated tissue injury through inhibiting ferroptosis in mice

Amifostine has been the only small molecule radio-protector approved by FDA for decades; however, the serious adverse effects limit its clinical use. To address the toxicity issues and maintain the good potency, a series of modified small polycysteine peptides had been prepared. Among them, compound 5 exhibited the highest radio-protective efficacy, the same as amifostine, but much better safety profile. To confirm the correlation between the radiation-protective efficacy and the DNA binding capability, each of the enantiomers of the polycysteine peptides had been prepared. As a result, the l-configuration compounds had obviously higher efficacy than the corresponding d-configuration enantiomers; among them, compound 5 showed the highest DNA binding capability and radiation-protective efficacy. To our knowledge, this is the first study that has proved their correlations using direct comparison. Further exploration of the mechanism revealed that the ionizing radiation (IR) triggered ferroptosis inhibition by compound 5 could be one of the pathways for the protection effect, which was different from amifostine. In summary, the preliminary result showed that compound 5, a polycysteine as a new type of radio-protector, had been developed with good efficacy and safety profile. Further study of the compound for potential use is ongoing.

Tripeptide-induced modulation of mesenchymal stem cell biomechanics stimulates proliferation and wound healing

We demonstrate the ability of two tripeptides to promote proliferation and modulate the mechanical properties of human mesenchymal stem cells (hMSCs). Notably, Young's modulus of peptide-treated hMSCs was found to be ～2 fold higher compared to the control group. These peptides promoted wound healing in hMSCs, without stimulating osteogenic and adipogenic differentiation, thus showing high potential in vascular tissue engineering applications.

Initial Analysis of the Arylomycin D Antibiotics

The arylomycins are a class of natural product antibiotics that inhibit bacterial type I signal peptidase and are under development as therapeutics. Four classes of arylomycins are known, arylomycins A-D. Previously, we reported the synthesis and analysis of representatives of the A, B, and C classes and showed that their spectrum of activity has the potential to be much broader than originally assumed. Along with a comparison of the mechanism of acquired and innate resistance, this led us to suggest that the arylomycins are latent antibiotics, antibiotics that once possessed broad-spectrum activity, but which upon examination today, have only narrow spectrum activity due to prior selection for resistance in the course of the competition with other microorganisms that drove their evolution in the first place. Interestingly, actinocarbasin, the only identified member of the arylomycin D class, has been reported to have activity against MRSA. To confirm and understand this activity, several actinocarbasin derivatives were synthesized. We demonstrate that the previously reported structure of actinocarbasin is incorrect, identify what is likely the correct scaffold, confirm that scaffold has activity against MRSA, and determine the origin of this activity.

Aminothiol compound, preparation method of aminothiol compound and application of aminothiol compound in radiation protection

The invention discloses an aminothiol compound, a preparation method of the aminothiol compound and application of the aminothiol compound in radiation protection. The compound has a structure shown in the formula I in the description, wherein A1 is selected from -C(O)NR8-, -S(O)2-NR8-, -S(O)NR8- and -R7-NR8-, A2 is selected from carbonyl, sulfonyl, sulfinyl and substituted or unsubstituted C1-6 alkyl, R1, R2, R5 and R6 can be the same or not and are selected from hydrogen and substituted or unsubstituted C1-C5 alkyl or hetero alkyl, n is an integer from 0 to 20000, R3 and R4 are independently selected from hydrogen, X and substituted or unsubstituted C1-6 alkyl, X is selected from F, Cl, Br and I, R7 is selected from substituted or unsubstituted C1-C6 alkyl, and R8 is selected from hydrogen and substituted or unsubstituted C1-C6 alkyl. The compound has the effect of reducing biological injury caused by ionizing radiation and also has the effects of prolonging the lifetime of radiated animals and increasing the survival rate of the radiated animals.

Multifunctional imaging cross-linked stable nanometer drug-loading micelles and preparation method thereof

The present invention discloses multifunctional imaging cross-linked stable nanometer drug-loading micelles and a preparation method thereof. The preparation method comprises: adding 200 mg of an amphiphilic drug carrier mPEG-S-Trityl-Cys-Dopa and a hydrophobic anti-cancer drug to an organic solvent, dissolving, and carrying out dialysis by using a dialysis bag to remove free Fe; carrying out centrifugation, and filtering the supernatant by using a 0.45 [mu]m microporous filtration membrane; and carrying out freeze drying on the filtrate, wherein the freeze-dried product is the multifunctional imaging cross-linked stable nanometer drug-loading micelles mPEG-S-Trityl-Cys-Dopa-Fe/hydrophobic anti-cancer drug. According to the present invention, the obtained nanometer micelles have the stability and the pH-sensitivity, and can be visible by MRI, can break through the single-function mode of the traditional drug delivery system, can integrate the MRI imaging function and the drug carrier function, and can achieve the synchronous diagnosis and treatment of cancers.

PROCESS FOR PREPARING EPTIFIBATIDE

The present invention provides processes for preparation of eptifibatide that involve coupling of amino acids in a (2+5), (4+3) and (3+4) sequence method. The invention further provides products produced by the described processes, novel compounds that can be used as synthetic intermediates for the preparation of eptifibatide.

A tetrazine templated method for the synthesis of ternary conjugates

Conjugation is an important reaction that enables coupling of molecules. Many protocols exist for the synthesis of binary conjugates from two different molecules or for the polyvalent display of a single molecule. There aren't many methods for the synthesis of ternary conjugates. However, methods for ternary conjugation are important for understanding the interplay of interactions between three biomolecules (or any three molecules per se). A strategy for ternary bioconjugation using inverse electron demand Diels-Alder reaction with tetrazine is studied. Ternary conjugation was demonstrated by the reaction of a model glyco-peptide binary conjugate with a fluorescent tagged olefin. The Royal Society of Chemistry 2013.

Novel molecular combination deriving from natural aminoacids and polyphenols: Design, synthesis and free-radical scavenging activities

Following the recent output of scientific publications in the matter of synergic activity between different antioxidants, we have undertaken the present study with the aim to synthesize new molecules with radical-scavengers activity based on the conjugation of bioactive portions (i.e. phenols, cysteine, methionine or tyrosine), characterized by different structures and mechanisms of action, to promote the simultaneous quenching of different radical species in the site of the oxidative damage. In this context, derivatives of phenolic acid, aminoacids and dopamine have been also prepared. The newly synthesized compounds were evaluated in vitro applying specific and complementary antioxidant test such as DPPH assay and ORAC test. As emerged from the evaluation, prerequisites for the activity of the synthesized molecules were: i) the maintenance of at least two hydroxylic groups on the aromatic moiety of phenolic portion, ii) the presence of a spacer between the aromatic moiety and the carbonilic group.

CYSTEINE AND CYSTINE BIOISOSTERES TO TREAT SCHIZOPHRENIA AND REDUCE DRUG CRAVINGS

The present invention provides cysteine and cystine bioisosteres for the treatment of schizophrenia and drug addiction. The invention further encompasses pharmaceutical compositions containing such bioisosteres and methods of using the bioisosteres for treatment of schizophrenia and drug addiction.