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Carbamic acid is the compound with the formula NH₂COOH. The attachment of the acid group to a nitrogen or amine (instead of carbon) distinguishes it from carboxylic acid and an amide. Many derivatives and analogues of carbamic acid are known. They are generally unstable, reverting to the parent amine and carbon dioxide.^[1] The deprotonated anion (or conjugate base) of this functional group is a carbamate. Carbamic acid is a planar molecule.^[2]

Occurrence

Carbamic acid is an intermediate in the production of urea, which involves the reaction of carbon dioxide and ammonia.^[3]

CO₂ + NH₃ → H₂N-CO₂H

H₂N-CO₂H + NH₃ → CO(NH₂)₂ + H₂O

"Carbamoyltransferases" are transferase enzymes classified under EC number 2.1.3.

Derivatives of carbamic acid

carbamic acid group
carbamate group
carbamoyl group
carbamoyl chloride group

Carbamic acids are intermediates in the decomposition of carbamate protecting groups; the hydrolysis of an ester bond produces carbamic acid the evolution of carbon dioxide drives the deprotection reaction forward, yielding the unprotected amine.

Carbamates usually refer to esters of carbamic acid. Methyl carbamate is the simplest ester of carbamic acid. Unlike carbamic acids, the esters are stable. They are prepared by reaction of carbamoyl chlorides with alcohols, the addition of alcohols to isocyanates, and the reaction of carbonate esters with ammonia.^[4]

Some esters have use as muscle relaxants which bind to the barbiturate site of the GABA_A receptor,^[5] while others are used as insecticides, for example aldicarb.^[6]

References

^ Thomas L. Lemke. (2003). Review of organic functional groups : introduction to medicinal organic chemistry. Philadelphia, Pa.: Lippincott Williams & Wilkins. p. 63. ISBN 978-0-7817-4381-5.
^ R.K. Khanna; M.H. Moore. (1998). "A 55". Carbamic acid: molecular structure and IR spectra (pii: S1386-1425(98)00228-5) (PDF). Greenbelt, MD.: Elsevier. pp. 961–967.
^ Meessen, J. H.; Petersen, H. (2005), "Urea", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a27_333
^ Peter Jäger, Costin N. Rentzea and Heinz Kieczka "Carbamates and Carbamoyl Chlorides" in Ullmann's Encyclopedia of Industrial Chemistry, 2012, Wiley-VCH, Weinheim. doi:10.1002/14356007.a05_051
^ John H. Block; John M. Beale, eds. (2004). "Central Nervous System Depressant". Wilson and Gisvold's textbook of organic medicinal and pharmaceutical chemistry. Philadelphia, Pa.: Lippincott Williams & Wilkins. p. 495. ISBN 978-0-7817-3481-3.
^ Risher, JF; Mink, FL; Stara, JF (1987). "The toxicologic effects of the carbamate insecticide aldicarb in mammals: a review". Environmental Health Perspectives. 72: 267–81. doi:10.2307/3430304. JSTOR 3430304. PMC 1474664. PMID 3304999.

UpToDate Contents

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1. 尿素サイクル障害：管理 urea cycle disorders management
2. 有機酸血症 organic acidemias
3. バルプロ酸中毒 valproic acid poisoning
4. 新生児の持続性肺高血圧症 persistent pulmonary hypertension of the newborn

English Journal

Novel Pathogenic Variant (c.580C>T) in the CPS1 Gene in a Newborn With Carbamoyl Phosphate Synthetase 1 Deficiency Identified by Whole Exome Sequencing.

Choi R1, Park HD2, Yang M1, Ki CS1, Lee SY1, Kim JW1, Song J3, Chang YS4,5, Park WS4,6.
Annals of laboratory medicine.Ann Lab Med.2017 Jan;37(1):58-62. doi: 10.3343/alm.2017.37.1.58.
Diagnosis of the urea cycle disorder (USD) carbamoyl-phosphate synthetase 1 (CPS1) deficiency (CPS1D) based on only the measurements of biochemical intermediary metabolites is not sufficient to properly exclude other UCDs with similar symptoms. We report the first Korean CPS1D patient using whole ex
PMID 27834067

Novel urea and bis-urea primaquine derivatives with hydroxyphenyl or halogenphenyl substituents: Synthesis and biological evaluation.

Perković I1, Antunović M2, Marijanović I2, Pavić K1, Ester K3, Kralj M3, Vlainić J3, Kosalec I4, Schols D5, Hadjipavlou-Litina D6, Pontiki E6, Zorc B7.
European journal of medicinal chemistry.Eur J Med Chem.2016 Nov 29;124:622-636. doi: 10.1016/j.ejmech.2016.08.021. Epub 2016 Aug 24.
A series of novel compounds 3a-j and 6a-j with primaquine and hydroxyl or halogen substituted benzene moieties bridged by urea or bis-urea functionalities were designed, synthesized and evaluated for biological activity. The title compounds were prepared using benzotriazole as the synthon, through s
PMID 27614409

Association between the p.Thr1406Asn polymorphism of the carbamoyl-phosphate synthetase 1 gene and necrotizing enterocolitis: A prospective multicenter study.

Moonen RM1,2, Cavallaro G3, Huizing MJ2, González-Luis GE4, Mosca F3, Villamor E2.
Scientific reports.Sci Rep.2016 Nov 11;6:36999. doi: 10.1038/srep36999.
The p.Thr1406Asn (rs1047891) polymorphism of the carbamoyl-phosphate synthetase 1 (CPS1) gene has been linked to functional consequences affecting the downstream availability of the nitric oxide precursor L-arginine. L-arginine concentrations are decreased in preterm infants with necrotizing enteroc
PMID 27833157

Japanese Journal

Synthesis and Evaluation of 1H-Pyrrolo[2,3-b]pyridine Derivatives as Novel Immunomodulators Targeting Janus Kinase 3

Chemical and Pharmaceutical Bulletin 63(5), 341-353, 2015
NAID 130005067249

Synthesis and Evaluation of 1H-Pyrrolo[2,3-b]pyridine Derivatives as Novel Immunomodulators Targeting Janus Kinase 3

Chemical and Pharmaceutical Bulletin advpub(0), 2015
NAID 130004803789

Synthesis of Spirooxindoles from Carbamoyl Chlorides via Cyclopropyl Methine C(sp^3)-H Activation Using Palladium Catalyst

Chemistry letters 42(7), 753-755, 2013-07-05
NAID 10031183283

「カルバミン酸」

Carbamic acid
Names
	IUPAC name Carbamic acid
	Other names Aminomethanoic Acid
Identifiers
CAS Number	463-77-4
3D model (Jmol)	Interactive image
ChEBI	CHEBI:28616
ChEMBL	ChEMBL125278
ChemSpider	271
DrugBank	DB04261
KEGG	C01563
MeSH	Carbamic+acid
PubChem	277
	InChI InChI=1S/CH3NO2/c2-1(3)4/h2H2,(H,3,4) Key: KXDHJXZQYSOELW-UHFFFAOYSA-N ; InChI=1/CH3NO2/c2-1(3)4/h2H2,(H,3,4) Key: KXDHJXZQYSOELW-UHFFFAOYAC ;
	SMILES O=C(O)N ;
Properties
Chemical formula	CH3NO2
Molar mass	61.040 g/mol
Related compounds
Related compounds	Formamide; Dithiocarbamate; Carbonic acid; Urea; Ethyl carbamate; Glycine
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

　　[★]

英: carbamate
関: カルバモイル carbamoyl、カルバモイルリン酸、尿素サイクル

NH₂-COOH (FB.418)

同: carbamate

「カルバモイル」

　　[★]

英: carbamoyl

カルバミン酸からヒドロキシ基をのぞくことにより得られる基

NH₂CO-

「carbamoyl-phosphate synthase」

　　[★]

カルバモイルリン酸合成酵素、カルバモイルリン酸シンターゼ

関: carbamoyl-phosphate synthetase、carbamoyl-phosphate synthetase I

「aspartate carbamoyltransferase」

　　[★]

アスパラギン酸カルバモイル基転移酵素、アスパラギン酸カルバモイルトランスフェラーゼ

関: aspartate transcarbamylase

「glutamine-hydrolyzing carbamoyl-phosphate synthase」

　　[★]

グルタミン加水分解性カルバモイルリン酸合成酵素、グルタミン加水分解性カルバモイルリン酸シンターゼ

「ornithine carbamoyl transferase」

　　[★] オルニチンカルバモイルトランスフェラーゼ

「carbamoyl-phosphate synthetase」

　　[★] カルバモイルリン酸合成酵素

[1] Thomas L. Lemke. (2003). Review of organic functional groups : introduction to medicinal organic chemistry. Philadelphia, Pa.: Lippincott Williams & Wilkins. p. 63. ISBN 978-0-7817-4381-5.

[2] R.K. Khanna; M.H. Moore. (1998). "A 55". Carbamic acid: molecular structure and IR spectra (pii: S1386-1425(98)00228-5) (PDF). Greenbelt, MD.: Elsevier. pp. 961–967.

[Ullmann-3] Meessen, J. H.; Petersen, H. (2005), "Urea", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a27_333

[4] Peter Jäger, Costin N. Rentzea and Heinz Kieczka "Carbamates and Carbamoyl Chlorides" in Ullmann's Encyclopedia of Industrial Chemistry, 2012, Wiley-VCH, Weinheim. doi:10.1002/14356007.a05_051

[5] John H. Block; John M. Beale, eds. (2004). "Central Nervous System Depressant". Wilson and Gisvold's textbook of organic medicinal and pharmaceutical chemistry. Philadelphia, Pa.: Lippincott Williams & Wilkins. p. 495. ISBN 978-0-7817-3481-3.

[6] Risher, JF; Mink, FL; Stara, JF (1987). "The toxicologic effects of the carbamate insecticide aldicarb in mammals: a review". Environmental Health Perspectives. 72: 267–81. doi:10.2307/3430304. JSTOR 3430304. PMC 1474664. PMID 3304999.

リンク元	「カルバミン酸」「カルバモイル」
拡張検索	「carbamoyl-phosphate synthase」「aspartate carbamoyltransferase」「glutamine-hydrolyzing carbamoyl-phosphate synthase」「ornithine carbamoyl transferase」「carbamoyl-phosphate synthetase」

匿名

検索

案内

案内

carbamoyl