trans-2-Hexenoyl-CoA

Base Information

• Chemical Name: trans-2-Hexenoyl-CoA
• CAS No.: 10018-93-6
• Molecular Formula: C₂₇H₄₄N₇O₁₇P₃S
• Molecular Weight: 863.67
• Nikkaji Number: J2.755.178E
• Mol file: 10018-93-6.mol

Synonyms:trans-2-Hexenoyl-CoA;SCHEMBL21978091;(2E)-Hexenoyl-CoA;(Acyl-CoA);[M+H]+

Chemical Property of trans-2-Hexenoyl-CoA

Chemical Property:

• PSA: 418.36000
• LogP: 1.38400
• XLogP3: -3.8
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 22
• Rotatable Bond Count: 23
• Exact Mass: 863.17272513
• Heavy Atom Count: 55
• Complexity: 1490

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC=CC(=O)SCCNC(=O)CCNC(=O)C(C(C)(C)COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)O
• Isomeric SMILES: CCC/C=C/C(=O)SCCNC(=O)CCNC(=O)C(C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)O

Technology Process of trans-2-Hexenoyl-CoA

There total 13 articles about trans-2-Hexenoyl-CoA 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: 71.0%

coenzyme A (85-61-0) + S-phenyl (E)-hex-2-enethioate → (2E)-hexenoyl-coenzyme A (6701-39-9,10018-93-6)

Guidance literature:

With sodium hydrogencarbonate; sodium hydroxide; In tetrahydrofuran; at 0 - 4 ℃; pH=8;

DOI:10.1074/jbc.M115.677195

Reference yield:

S-hexanoyl-coenzyme-A (5060-32-2,21708-76-9) → (2E)-hexenoyl-coenzyme A (6701-39-9,10018-93-6)

Guidance literature:

With ferrocenium hexafluorophosphate; short chain acyl-CoA dehydrogenase PP₂₂₁₆ from Pseudomonas putida KT₂₄₄₀; In aq. phosphate buffer; at 25 ℃; for 2h; pH=7.2; Enzymatic reaction;

DOI:10.1021/jacs.9b09187

Reference yield:

(E)-2-Hexenoic acid (13419-69-7) → (2E)-hexenoyl-coenzyme A (6701-39-9,10018-93-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / dichloromethane / 0.5 h / 20 °C

1.2: 2 h / 4 °C / Inert atmosphere

2.1: potassium hydrogencarbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C

With potassium hydrogencarbonate; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/bi300879n

upstream raw materials:

coenzyme A

trans-3-hexenoylcoenzyme A

(E)-2-Hexenoic acid

C₉H₁₄O₄

Downstream raw materials:

S-hexanoyl-coenzyme-A

(E)-2-Hexenoic acid

Refernces

• 1、 Sandy, Moriah,Rui, Zhe,Gallagher, Joe,Zhang, Wenjun. "Enzymatic synthesis of dilactone scaffold of antimycins". . p. 1956 - 1961. Retrieved 2012.
• 2、 Miyazawa, Takeshi,Takahashi, Shunji,Kawata, Akihiro,Panthee, Suresh,Hayashi, Teruo,Shimizu, Takeshi,Nogawa, Toshihiko,Osada, Hiroyuki. "Identification of middle chain fatty Acyl-CoA Ligase responsible for the biosynthesis of 2-alkylmalonyl-CoAs for Polyketide extender unit". . p. 26994 - 27011. Retrieved 2015.
• 3、 Wu, Long,Zeng, Jia,Deng, Guisheng,Guo, Fei,Li, Nan,Liu, Xiaojun,Chu, Xiusheng,Li, Ding. "Inactivation of thiolase by 2-alkynoyl-CoA via its intrinsic isomerase activity". . p. 3877 - 3880. Retrieved 2007.