Fomc-cis-L-hydroxyproline-OH

Base Information

• Chemical Name: Fomc-cis-L-hydroxyproline-OH
• CAS No.: 189249-10-3
• Molecular Formula: C20H19NO5
• Molecular Weight: 353.375
• Mol file: 189249-10-3.mol

Synonyms:Fmoc-4-(phosphonomethyl)-Phe-OH;(2S,4S)-N-Fmoc-4-hydroxyproline;N-fmoc-cis-4-hydroxy-L-proline;N-Fmoc-L-Pmp;Fmoc-4-phosphonomethylphenylalanine;Fmoc-L-4-Phosphonomethylphenylalanine;

Chemical Property of Fomc-cis-L-hydroxyproline-OH

Chemical Property:

• PSA: 87.07000
• LogP: 2.39320
• Storage Temp.: 2-8°C

Purity/Quality:

99%+, ^*data from raw suppliers

Fmoc-(2S,4S)-(-)-4-hydroxypyrrolidine-2-carboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Fomc-cis-L-hydroxyproline-OH

There total 5 articles about Fomc-cis-L-hydroxyproline-OH 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: 100.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + hydroxy L-proline (618-27-9,30724-02-8) → (4S)-Nα-Fmoc-4-hydroxy-L-proline (189249-10-3)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/ja5033277

Reference yield:

L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → (4S)-Nα-Fmoc-4-hydroxy-L-proline (189249-10-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium L-ascorbate; α-ketoglutaric acid disodium salt; ferrous(II) sulfate heptahydrate / aq. phosphate buffer / 30 °C / pH 7.5 / Enzymatic reaction

2: aq. phosphate buffer; acetonitrile / 37 °C / pH 7.5

With ferrous(II) sulfate heptahydrate; sodium L-ascorbate; α-ketoglutaric acid disodium salt; In aq. phosphate buffer; acetonitrile;

DOI:10.1021/acs.oprd.1c00405

Reference yield:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + hydroxy L-proline (618-27-9,30724-02-8) → (4S)-Nα-Fmoc-4-hydroxy-L-proline (189249-10-3)

Guidance literature:

hydroxy L-proline; With sodium hydrogencarbonate; In water; for 0.0833333h;

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide; In 1,4-dioxane; water; at 20 ℃; for 12h;

DOI:10.1002/chem.201901888

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

hydroxy L-proline

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

L-proline

Downstream raw materials:

N-(9-fluorenylmethoxycarbonyl)-(2S,4S)-4-tert-butoxyproline

C₄₆H₇₁N₁₁O₁₂S₂

[1-benzyl-2-(4-tert-butoxy-2-methylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

Refernces

• 1、 Dussauge, Solene,Moore, Charles,Snajdrova, Radka,Tassano, Erika,Vargas, Alexandra. "Discovery of New Fe(II)/α-Ketoglutarate-Dependent Dioxygenases for Oxidation of l-Proline". supporting information. . Retrieved 2022/02/09.
• 2、 Karunaratne, Chamini V.,Weldeghiorghis, Thomas K.,West, Christopher M.,Taylor, Carol M.. "Conformational changes associated with post-translational modifications of pro143 in Skp1 of dictyostelium -a dipeptide model system". supporting information. p. 15170 - 15175. Retrieved 2015/02/19.