[ CAS No. 127-17-3 ] {[proInfo.proName]}

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Quality Control of [ 127-17-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 127-17-3 ]

SDS Specification

Alternatived Products of [ 127-17-3 ]

Product Citations Expand+

An Azapeptide Platform in Conjunction with Covalent Warheads to Uncover High-Potency Inhibitors for SARS-CoV-2 Main Protease

Khatua, Kaustav ; Alugubelli, Yugendar R. ; Yang, Kai S. , et al. bioRxiv,2023.04.11.536467. DOI: 10.1101/2023.04.11.536467

Abstract: Main protease (MPro) of SARS-CoV-2, the viral pathogen of COVID-19, is a crucial nonstructural protein that plays a vital role in the replication and pathogenesis of the virus. Its protease function relies on three active site pockets to recognize P1, P2, and P4 amino acid residues in a substrate and a catalytic cysteine residue for catalysis. By converting the P1 Cα atom in an MPro substrate to nitrogen, we showed that a large variety of azapeptide inhibitors with covalent warheads targeting the MPro catalytic cysteine could be easily synthesized. Through the characterization of these inhibitors, we identified several highly potent MPro inhibitors. Specifically, one inhibitor, MPI89 that contained an aza-2,2-dichloroacetyl warhead, displayed a 10 nM EC50 value in inhibiting SARS-CoV-2 from infecting ACE2+ A549 cells and a selectivity index of 875. The crystallog. analyses of MPro bound with 6 inhibitors, including MPI89, revealed that inhibitors used their covalent warheads to covalently engage the catalytic cysteine and the aza-amide carbonyl oxygen to bind to the oxyanion hole. MPI89 represents one of the most potent MPro inhibitors developed so far, suggesting that further exploration of the azapeptide platform and the aza-2,2-dichloroacetyl warhead is needed for the development of potent inhibitors for the SARS-CoV-2 MPro as therapeutics for COVID-19.

Purchased from AmBeed: 5669-19-2 ; 1149-26-4 ; 7304-32-7 ; 16966-09-9 ; 3590-48-5 ; 38377-38-7 ; 848133-35-7 ; 103260-65-7 ; 27746-99-2 ; 51021-87-5 ; 127-17-3 ; 540750-29-6 ; 40056-18-6 ; 5704-66-5

Electrosynthesis of amino acids from biomass-derived α-hydroxyl acids

Kaili Yan ; Morgan L. Huddleston ; Brett A. Gerdes , et al. Green Chem.,2022,24(13):5320-5325. DOI: 10.1039/D2GC01779B

Abstract: Electrochemical conversion of biomass-derived intermediate compounds to high-value products has emerged as a promising approach in the field of biorefinery. Biomass upgrading allows for the production of chemicals from non-fossil-based carbon sources and capitalization on electricity as a green energy input. Amino acids, as products of biomass upgrading, have received relatively little attention. Pharmaceutical and food industries will benefit from an alternative strategy for the production of amino acids that does not rely on inefficient fermentation processes. The use of renewable biomass resources as starting materials makes this proposed strategy more desirable. Herein, we report an electrochemical approach for the selective oxidation of biomass-derived α-hydroxyl acids to α-keto acids, followed by electrochemical reductive amination to yield amino acids as the final products. Such a strategy takes advantage of both reactions at the anode and cathode and produces amino acids under ambient conditions with high energy efficiency. A flow electrolyzer was also successfully employed for the conversion of α-hydroxyl acids to amino acids, highlighting its great potential for large-scale application.

Purchased from AmBeed: 611-73-4 ; 2835-06-5 ; 302-72-7 ; 61-90-5 ; 56-40-6 ; 156-06-9 ; 90-64-2 ; 298-12-4 ; 498-36-2 ; 79-14-1 ; 127-17-3 ; 828-01-3 ; 50-21-5 ; 816-66-0

Product Details of [ 127-17-3 ]

CAS No. :	127-17-3	MDL No. :	MFCD00002585
Formula :	C₃H₄O₃	Boiling Point :	-
Linear Structure Formula :	CH₃C(O)COOH	InChI Key :	LCTONWCANYUPML-UHFFFAOYSA-N
M.W :	88.06	Pubchem ID :	1060
Synonyms :	Acetylformic acid	Chemical Name :	2-Oxopropanoic acid

Calculated chemistry of [ 127-17-3 ] Expand+

Physicochemical Properties

Num. heavy atoms :	6
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.33
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	18.51
TPSA :	54.37 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.07 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.25
Log Po/w (XLOGP3) :	-0.33
Log Po/w (WLOGP) :	-0.34
Log Po/w (MLOGP) :	-0.96
Log Po/w (SILICOS-IT) :	-0.48
Consensus Log Po/w :	-0.37

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-0.11
Solubility :	68.0 mg/ml ; 0.773 mol/l
Class :	Very soluble
Log S (Ali) :	-0.35
Solubility :	39.3 mg/ml ; 0.446 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	0.51
Solubility :	286.0 mg/ml ; 3.25 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Safety of [ 127-17-3 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	3265
Hazard Statements:	H227-H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 127-17-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 127-17-3 ]
Downstream synthetic route of [ 127-17-3 ]

[ 127-17-3 ] Synthesis Path-Upstream 1~4

1
[ 123-30-8 ]
[ 127-17-3 ]
[ 50741-53-2 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1957, vol. 607, p. 92,101
[2] Arkiv foer Kemi, 1953, vol. 5, p. 251,252[3] Justus Liebigs Annalen der Chemie, 1952, vol. 578, p. 188,193

2
[ 64-17-5 ]
[ 123-30-8 ]
[ 127-17-3 ]
[ 50741-53-2 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1957, vol. 607, p. 92,101

3
[ 100-48-1 ]
[ 127-17-3 ]
[ 37398-49-5 ]

Reference： [1] Journal of Organic Chemistry, 1991, vol. 56, # 8, p. 2866 - 2869

4
[ 127-17-3 ]
[ 211308-81-5 ]
[ 800401-84-7 ]

Reference： [1] Patent: WO2006/59164, 2006, A2, . Location in patent: Page/Page column 21
[2] Patent: WO2004/104001, 2004, A2, . Location in patent: Page 51

[ 127-17-3 ] Synthesis Path-Downstream 1~10

1
[ 6972-82-3 ]
[ 127-17-3 ]
[ 2625-22-1 ]

Reference： [1]Chemische Berichte,1908,vol. 41,p. 3964

2
[ 1450-93-7 ]
[ 127-17-3 ]
[ 53823-11-3 ]

Reference： [1]Tetrahedron Letters,1992,vol. 33,p. 4385 - 4388

3
[ 497-09-6 ]
[ 127-17-3 ]
(2S,5S)-2,4,5-Trihydroxy-tetrahydro-pyran-2-carboxylic acid [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,1995,vol. 6,p. 863 - 866

4
[ 29289-13-2 ]
[ 127-17-3 ]
[ 10241-97-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 4385 - 4388

5
[ 1415337-75-5 ]
[ 127-17-3 ]
[ 1118-69-0 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 10835 - 10845

6
[ 55589-47-4 ]
[ 127-17-3 ]
(1R,3S)-1,3-dihydroxy-8-methyl-2,3-dihydro-1H-indolizin-4-ium-3-carboxylate [ No CAS ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 14532 - 14539

7
[ 35661-51-9 ]
[ 127-17-3 ]
C₁₈H₁₆N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	In ethanol; at 20℃; for 24.5h;	Pyruvic acid (1.9 ml, 0.027 mol) was added to avessel containing a suspension of Fmoc-NH-NH2 (6.9 g, 0.027 mol) in absoluteethanol (42 ml). The reaction mixture was stirred for 30 min and then pyruvicacid (0.2 equiv) was added. The mixture was shaken for 24 h at roomtemperature. Solvent was evaporated under reduced pressure and theproduct was triturated with MTBE, filtered, dried in vacuo and purified byrecrystallization from isopropyl alcohol. The yield was 7.2 g (82percent). 1H NMR(400 MHz, CDCl3, ppm): 2.06 (s, 3H), 4.28 (t, 1H, J = 5.9 Hz), 4.69 (d, 2H,J = 5.9 Hz), 7.34 (t, 2H, J = 7.42 Hz), 7.43 (t, 2H, J = 7.42 Hz), 7.59 (d, 2H,J = 7.54 Hz), 7.79 (d, 2H, J = 8 Hz), 8.17 (s, 1H). MS (ESI, m/z). Calcd forC18H16N2O4: 324.11; Found 347.1 [M+Na]+.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 619 - 622

8
[ 16600-92-3 ]
[ 127-17-3 ]

Reference： [1]RSC Advances,2015,vol. 5,p. 66239 - 66259

9
[ 26787-78-0 ]
[ 3973-08-8 ]
[ 740742-98-7 ]
[ 64-18-6 ]
[ 79-14-1 ]
[ 110-94-1 ]
[ 124-04-9 ]
[ 80-69-3 ]
[ 473-81-4 ]
[ 471-47-6 ]
[ 110-15-6 ]
[ 1378848-02-2 ]
[ 15573-67-8 ]
C₉H₁₀N₂O₄ [ No CAS ]
C₉H₁₂N₂O₅S [ No CAS ]
C₈H₁₀N₂O₆S [ No CAS ]
C₉H₁₄N₂O₇S [ No CAS ]
C₉H₁₂N₂O₆S [ No CAS ]
C₈H₁₀N₂O₄S [ No CAS ]
C₁₀H₁₂N₂O₇S [ No CAS ]
C₁₅H₂₁N₃O₄S [ No CAS ]
C₁₅H₁₈N₂O₄S [ No CAS ]
C₁₄H₂₁N₃O₃S [ No CAS ]
C₈H₁₂N₂O₄S [ No CAS ]
C₈H₁₀N₂O₅S [ No CAS ]
C₆H₁₀O₇S [ No CAS ]
C₆H₇NO₄S [ No CAS ]
C₆H₁₁NO₃S [ No CAS ]
C₆H₉NO₃S [ No CAS ]
[ 144-62-7 ]
[ 64-19-7 ]
[ 802294-64-0 ]
[ 127-17-3 ]
[ 87-69-4 ]
[ 551-16-6 ]
[ 65-85-0 ]
[ 298-12-4 ]
2-hydroxy-3-(4-hydroxyphenyl)pyrazine [ No CAS ]
[ 6915-18-0 ]
[ 107-92-6 ]
[ 57457-65-5 ]
[ 99-96-7 ]

Reference： [1]Catalysis Today,2019

10
[ 527-07-1 ]
[ 849585-22-4 ]
[ 6338-41-6 ]
[ 127-17-3 ]

Yield	Reaction Conditions	Operation in experiment
3.4 mol; 4.7 mol; 13.11 mol	With lithium hydroxide; In water; at 180℃; under 7500.75 Torr; for 2h;Inert atmosphere;	For this example, neither the tungstate or the commercial ruthenium on carbon catalyst were used, and nitrogen was again used in place of hydrogen, except at a pressure of 1.0 MPa (150 psi). Full conversion of the substrate was experienced, with products including 1.29 weight percent of lactic acid (3.4 mol percent yield) of lactic acid, 4.8 weight percent of pyruvic acid (13.11 mol percent yield), and 0.3 weight percent of 5-hydroxymethyl-2-furancarboxylic acid (HMFCA)(4.7 mol percent yield) but no observable glycerol, ethylene glycol or propylene glycol

Reference： [1]Patent: WO2019/199540,2019,A1 .Location in patent: Paragraph 49-50

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Isomers

Technical Information

? Arndt-Eistert Homologation ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Bucherer-Bergs Reaction ? Clemmensen Reduction ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Fischer Indole Synthesis ? Grignard Reaction ? Heat of Combustion ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hunsdiecker-Borodin Reaction ? Hydride Reductions ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Preparation of Carboxylic Acids ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions of Carboxylic Acids ? Reformatsky Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

Historical Records

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H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 127-17-3 ] {[proInfo.proName]}

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[ 127-17-3 ] Synthesis Path-Upstream 1~4

[ 127-17-3 ] Synthesis Path-Downstream 1~10

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Aliphatic Chain Hydrocarbons

Ketones

Carboxylic Acids

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