5-[(3aR,4S,6aS)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid

Base Information

• Chemical Name: 5-[(3aR,4S,6aS)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid
• CAS No.: 58-85-5
• Deprecated CAS: 15720-24-8,22879-79-4,3672-05-7,58073-87-3
• Molecular Formula: C10H16N2O3S
• Molecular Weight: 244.315
• Hs Code.: 29362930
• DSSTox Substance ID: DTXSID7022679
• ChEMBL ID: CHEMBL1434820
• Mol file: 58-85-5.mol

Synonyms:157966-14-8;5-[(3aR,4S,6aS)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid;SCHEMBL5376391;(3aR,4S,6aS)-Hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanoic acid;CHEMBL1434820;NCGC00017315-02;NCGC00142422-01

Chemical Property of 5-[(3aR,4S,6aS)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 1.19E-14mmHg at 25°C
• Melting Point: 231-233 °C(lit.)
• Refractive Index: 90.5 ° (C=2, 0.1mol/L NaOH)
• Boiling Point: 573.6 °C at 760 mmHg
• PKA: 4.74±0.10(Predicted)
• Flash Point: 300.7 °C
• PSA: 103.73000
• Density: 1.267 g/cm³
• LogP: 1.45440
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: H2O: 0.2 mg/mL Solubility increases with addition of 1
• Water Solubility.: Soluble in hot water, dimethyl sulfoxide, alcohol and benzene.
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 244.08816355
• Heavy Atom Count: 16
• Complexity: 298

Purity/Quality:

98% ^*data from raw suppliers

Vitamin B7 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C2C(C(S1)CCCCC(=O)O)NC(=O)N2
• Isomeric SMILES: C1[C@@H]2[C@H]([C@@H](S1)CCCCC(=O)O)NC(=O)N2
• Description: Biotin is a water-soluble vitamin and serves as a coenzyme for five carboxylases.; It catalyzes key steps in the metabolism of fatty acids, glucose, and amino acids.
• Roles and Functions: Coenzyme for Carboxylases: Biotin is an essential cofactor for biotin-dependent enzymes, including carboxylases, decarboxylases, and transcarboxylases.; Metabolic Processes: It participates in gluconeogenesis, fatty acid synthesis, and amino acid metabolism.; Regulation of Gene Expression: Biotin regulates gene expression by biotinylation of lysine residues of histones H2A, H3, and H4.; Promotion of Cell Growth: Biotin promotes cell growth and is delivered into cells with high proliferation rates, including tumor cells.
• Structure: Chemical Structure: Biotin consists of a tetrahydroimidizalone ring fused with an organosulfur-containing tetrahydrothiophane ring that bears a valeric acid substituent.; Attachment to Enzymes: Biotin must be covalently attached to its cognate enzyme proteins, such as carboxylases, for function.
• Enzymatic Attachment: Attachment Process: The attachment of biotin to enzyme proteins is mediated by the formation of an amide linkage between the biotin carboxyl group and the 蔚-amino group of a specific lysine residue.; Catalyzed by Enzymes: This reaction is catalyzed by biotin protein ligase (BPL) in bacteria or holocarboxylase synthetase in animals.
• Health Implications: Deficiency: Severe biotin deficiency has been linked to birth defects, misdiagnosis of multiple sclerosis, and impaired immune function.; Markers for Deficiency: Reliable markers for biotin status include the activity of propionyl-CoA carboxylase and methylcrotonyl-CoA carboxylase.
• Uses: Drug Delivery Systems (DDSs): Biotin can be conjugated to different molecules via a valeric acid tail for biotinylation, facilitating drug delivery.; Functionalization of Nanocarriers: DDSs' surfaces may be biotin-functionalized through pre-conjugation or post-conjugation methods for targeted delivery.

Technology Process of 5-[(3aR,4S,6aS)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid

There total 284 articles about 5-[(3aR,4S,6aS)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.5%

(2S,3S,4S)-5-(3,4-diaminotetrahydrothiophen-2-yl)pentanoic acid + carbonic acid dimethyl ester (616-38-6) → biotin (58-85-5,22879-79-4)

Guidance literature:

With boron trifluoride diethyl etherate; tin(IV) chloride; at 150 ℃; for 3.5h; under 300.03 Torr; Temperature; Pressure; Reagent/catalyst; Autoclave;

Reference yield: 97.0%

(3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione (28092-52-6) + potassium thioacetate (10387-40-3) → biotin (58-85-5,22879-79-4)

Guidance literature:

In water; at 0 - 60 ℃; Temperature;

Reference yield: 95.8%

5-((3aR,6S,6aS)-1-Benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic acid → biotin (58-85-5,22879-79-4)

Guidance literature:

With hydrogenchloride; sodium dithionite; water; sodium hydroxide; In water; at 55 - 90 ℃; for 0.5h; Reagent/catalyst;

upstream raw materials:

phosgene

(2S,3S,4R)-cis-5-(3,4-diaminotetrahydro-2-thienyl)valeric acid

(+/-)-biotin

5-[(3aS)-1( oder !3)-benzyl-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl]-valeric acid

Downstream raw materials:

biotin

vitamin H

biotin-N-(1-propyl)amide

N²-benzyloxycarbonyl-N⁶-[5-((3aS)-2-oxo-(3ar,6ac)-hexahydro-thieno[3,4-d]imidazol-4t-yl)-pentanoyl]-L-lysine amide

Refernces

• 1、 -. "SYSTEMS AND METHODS FOR DETECTION OF TARGET ANALYTES USING SELECTIVELY CLEAVABLE BONDS". . . Retrieved 2021/09/10.
• 2、 Busto, Jesús H.,Jiménez-Osés, Gonzalo,Mazo, Nuria,Navo, Claudio D.,Peregrina, Jesús M.. "Selective modification of sulfamidate-containing peptides". supporting information. p. 6265 - 6275. Retrieved 2020/09/07.