Hydroxymethyl group
The hydroxymethyl group is a substituent with the structural formula −CH2−OH. It consists of a methylene bridge (−CH2− unit) bonded to a hydroxyl group (−OH). This makes the hydroxymethyl group a primary alcohol. It is a constitutional isomer of the methoxy group (−O−CH3), differing only in the attachment site and orientation to the rest of the molecule. However, their chemical properties are different for an alcohol as opposed to an ether.[1][2]
All primary alcohols feature a hydroxymethyl group, but often the term is reserved for compounds where the point of attachment is not CH2 nor even CH. A major exception to this pattern is the description of several sugars as containing hydroxymethyl groups.
Occurrence
[edit]Organic chemistry
[edit]Nature
[edit]
Hydroxymethyl is the side chain of encoded amino acid serine.[3] This hydroxymethyl group is the site of many post-translational modifications.
Many sugars and carbohydrates feature hydroxymethyl groups, prominently C6 of glucose and mannose, as well as both C1 and C6 of fructose. The partially dehydrated derivative of fructose, hydroxymethylfurfural retains the hydroxymethyl group affixed to a furan ring.
Pyridoxine, the precusor to vitamin B6, features two hydroxymethyl groups on a pyridine ring.
Industrial and laboratory chemicals
[edit]Many commercial polyols are hydroxymethyl compounds: pentaerythritol, trimethylolpropane, and methylolurea. Taking advantage of their multifunctionality, polymer cross-linking is their typical application.
Tris(hydroxymethyl)aminomethane, also known as "tris", is a common buffering agent.
Main group chemistry
[edit]Hydroxymethyl groups are pervasive in heteroatom and main group chemistry. Tris(hydroxymethyl)phosphine is one such example.
Preparation
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Typically, hydroxymethylation is achieved by the addition of formaldehyde to substrates bearing an "active" proton. For example, terminal alkynes add formaldehyde:[4]
- RC≡CH + CH2O → RC≡CCH2OH
Hydroxymethyl groups arise by hydroxylation of methoxy groups. This conversion enables demethylation of the herbicide dicamba.[5]
References
[edit]- ↑ NAMING ORGANIC COMPOUNDS (PDF). p. 37. Archived from the original (PDF) on 2022-07-21. Retrieved 2022-08-08.
- ↑ Dong, Hao; Zheng, Erjin; Niu, Zhiyin; Zhang, Xiaoyu; Lin, Yi-Yu; Jain, Priyesh; Yu, Qiuming (2020-04-15). "Hydroxymethyl-Functionalized PEDOT-MeOH:PSS for Perovskite Solar Cells". ACS Applied Materials & Interfaces. 12 (15): 17571–17582. doi:10.1021/acsami.0c01756. ISSN 1944-8252. PMID 32204591. S2CID 214630308.
- ↑ Perczel, András; Farkas, Ödön; Csizmadia, Imre G. (1996-01-01). "Peptide Models. 18. Hydroxymethyl Side-Chain Induced Backbone Conformational Shifts of L-Serine Amide. All ab Initio Conformers of For L-Ser-NH2". Journal of the American Chemical Society. 118 (33): 7809–7817. doi:10.1021/ja960464q. ISSN 0002-7863.
- ↑ John Hooz, Jorge Cabezas, Sergio Musmanni, Jose Calzada (1990). "Propargylation of Alkyl Halides: (E)-6,10-Dimethyl-5,9-Undecadien-1-Yne and (E)-7,11-Dimethyl-6,10-Dodecadien-2-Yn-1-Ol". Organic Syntheses. 69: 120. doi:10.15227/orgsyn.069.0120.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ↑ Dumitru, Razvan; Jiang, Wen Zhi; Weeks, Donald P.; Wilson, Mark A. (2009). "Crystal Structure of Dicamba Monooxygenase: A Rieske Nonheme Oxygenase that Catalyzes Oxidative Demethylation". Journal of Molecular Biology. 392 (2): 498–510. doi:10.1016/j.jmb.2009.07.021. PMC 3109874. PMID 19616011.
External links
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