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1509-35-9,MFCD00066445
Catalog No.:AA001MVA

1509-35-9 | D-Alloisoleucine

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Purity
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Price(USD)
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250mg
97%
in stock  
$8.00   $6.00
- +
1g
98%(HPLC)
in stock  
$24.00   $17.00
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5g
97%
in stock  
$42.00   $29.00
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10g
97%
in stock  
$72.00   $50.00
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25g
97%
in stock  
$145.00   $102.00
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100g
97%
in stock  
$579.00   $405.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA001MVA
Chemical Name:
D-Alloisoleucine
CAS Number:
1509-35-9
Molecular Formula:
C6H13NO2
Molecular Weight:
131.1729
MDL Number:
MFCD00066445
SMILES:
CC[C@@H]([C@H](C(=O)O)N)C
FEMA Number:
3295
Properties
Properties
 
BP:
225.8 °C at 760 mmHg  
Form:
Solid  
MP:
291 °C (dec.)(lit.)  
Refractive Index:
-37 ° (C=4, 6mol/L HCl)  
Storage:
Inert atmosphere;Room Temperature;  

Computed Properties
 
Complexity:
103  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Heavy Atom Count:
9  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
3  
XLogP3:
-1.7  

Downstream Synthesis Route
1509-35-9   
(2R,3S)-2-hydroxy-3-methylpentanoicacid 

[1]Locationinpatent:experimentalpartPettit,GeorgeR.;Hu,Shougang;Knight,JohnC.;Chapuis,Jean-Charles[JournalofNaturalProducts,2009,vol.72,#3,p.372-379]

[2]Dai,Lu;Chen,Bo;Lei,Honghui;Wang,Zhuo;Liu,Yuqing;Xu,Zhengshuang;Ye,Tao[ChemicalCommunications,2012,vol.48,#69,p.8697-8699]

[3]Winitzetal.[JournaloftheAmericanChemicalSociety,1956,vol.78,p.2423,2428]

[4]Kallmerten,James;Gould,ThomasJ.[JournalofOrganicChemistry,1986,vol.51,#7,p.1152-1155]

[5]Kurome,Toru;Inami,Kaoru;Inoue,Tetsuya;Ikai,Katsushige;Takesako,Kazutoh;Kato,Ikunoshin;Shiba,Tetsuo[Tetrahedron,1996,vol.52,#12,p.4327-4346]

[6]Ikeda,Yoshitaka;Nonaka,Hikaru;Furumai,Tamotsu;Igarashi,Yasuhiro[JournalofNaturalProducts,2005,vol.68,#4,p.572-573]

[7]Locationinpatent:experimentalpartSimmons,T.Luke;Engene,Niclas;Urena,LuisDavid;Romero,LuzI.;Ortega-Barria,Eduardo;Gerwick,Lena;Gerwick,WilliamH.[JournalofNaturalProducts,2008,vol.71,#9,p.1544-1550]

[8]Locationinpatent:experimentalpartChoi,Hyukjae;Pereira,AlbanR.;Cao,Zhengyu;Shuman,CynthiaF.;Engene,Niclas;Byrum,Tara;Matainaho,Teatulohi;Murray,ThomasF.;Mangoni,Alfonso;Gerwick,WilliamH.[JournalofNaturalProducts,2010,vol.73,#8,p.1411-1421]

[9]Tripathi,Ashootosh;Puddick,Jonathan;Prinsep,MicheleR.;Rottmann,Matthias;Tan,LikTong[JournalofNaturalProducts,2010,vol.73,#11,p.1810-1814]

[10]Locationinpatent:experimentalpartMevers,Emily;Liu,Wei-Ting;Engene,Niclas;Mohimani,Hosein;Byrum,Tara;Pevzner,PavelA.;Dorrestein,PieterC.;Spadafora,Carmenza;Gerwick,WilliamH.[JournalofNaturalProducts,2011,vol.74,#5,p.928-936]

[11]Locationinpatent:experimentalpartSimmons,T.Luke;Nogle,LisaM.;Media,Joseph;Valeriote,FrederickA.;Mooberry,SusanL.;Gerwick,WilliamH.[JournalofNaturalProducts,2009,vol.72,#6,p.1011-1016]Locationinpatent:experimentalpartThornburg,ChristopherC.;Thimmaiah,Muralidhara;Shaala,LamiaaA.;Hau,AndrewM.;Malmo,JayM.;Ishmael,JaneE.;Youssef,DiaaT.A.;McPhail,KerryL.[JournalofNaturalProducts,2011,vol.74,#8,p.1677-1685]

[12]Locationinpatent:experimentalpartTripathi,Ashootosh;Puddick,Jonathan;Prinsep,MicheleR.;Rottmann,Matthias;Chan,KokPing;Chen,DavidYu-Kai;Tan,LikTong[Phytochemistry,2011,vol.72,#18,p.2369-2375]

[13]Jia,Chao;Yang,Ke-Wu;Liu,Cheng-Cheng;Feng,Lei;Xiao,Jian-Min;Zhou,Li-Sheng;Zhang,Yi-Lin[BioorganicandMedicinalChemistryLetters,2012,vol.22,#1,p.482-484]

[14]Tan,KarenCo;Wakimoto,Toshiyuki;Abe,Ikuro[OrganicLetters,2014,vol.16,#12,p.3256-3259]

[15]Jamison,MatthewT.;Molinski,TadeuszF.[JournalofNaturalProducts,2016,vol.79,#9,p.2243-2249]

[16]Luo,Danmeng;Putra,MasteriaY.;Ye,Tao;Paul,ValerieJ.;Luesch,Hendrik[MarineDrugs,2019,vol.17,#2]

[17]Lim,Changjin[Molecules,2019,vol.24,#19]

[18]Kienle,Maryline;Eisenring,Patrick;Stoessel,Barbara;Horlacher,OliverP.;Hasler,Samuel;VanColen,Gwénaëlle;Hartkoorn,RubenC.;Vocat,Anthony;Cole,StewartT.;Altmann,Karl-Heinz[JournalofMedicinalChemistry,2020,vol.63,#3,p.1105-1131]

[19]Brumley,DavidA.;Chen,Qi-Yin;Gunasekera,SarathP.;Luesch,Hendrik;Paul,ValerieJ.[OrganicLetters,2020,vol.22,#11,p.4235-4239]

[1]Yajima,Tatsuo;Horikawa,Takao;Takeda,Nobuhiro;Takemura,Eri;Hattori,Hiroaki;Shimazaki,Yuichi;Shiraiwa,Tadashi[TetrahedronAsymmetry,2008,vol.19,#11,p.1285-1287]

[2]Greensteinetal.[BiochemicalPreparations,1951,vol.3,p.84,89]

[3]Cambie,Mara;D'Arrigo,Paola;Fasoli,Ezio;Servi,Stefano;Tessaro,Davide;Canevotti,Francesco;DelCorona,Lucio[TetrahedronAsymmetry,2003,vol.14,#20,p.3189-3196]

[4]Kato,Shin-Ichi;Oba,Yuichi;Ojika,Makoto;Inouye,Satoshi[Bioscience,BiotechnologyandBiochemistry,2006,vol.70,#6,p.1528-1532]

[5]Jamison,MatthewT.;Molinski,TadeuszF.[JournalofNaturalProducts,2016,vol.79,#9,p.2243-2249]

1509-35-9    108-24-7    64-19-7   
(2S,3S)-N-acetyl-2-amino-3-methylpentanoicacid 
  54831-20-8 

[1]Greensteinetal.[JournalofBiologicalChemistry,1951,vol.188,p.647,652][BiochemicalPreparations,1953,vol.3,p.84,87]

62210-73-5    1509-35-9   
N-benzyloxycarbonylamino-D-alloisoleucine 

[1]Li;Ewing;Harris;Joullie[JournaloftheAmericanChemicalSociety,1990,vol.112,#21,p.7659-7672]

[1]Tschaen,DavidM.;Turos,Edward;Weinreb,StevenM.[JournalofOrganicChemistry,1984,vol.49,#26,p.5058-5064]

Literature

Title: Substrate specificity of a peptidyl-aminoacyl-L/D-isomerase from frog skin.

Journal: Amino acids 20120501

Title: Synthesis of the amino acid conjugates of epi-jasmonic acid.

Journal: Amino acids 20120501

Title: Natural products from the Lithistida: a review of the literature since 2000.

Journal: Marine drugs 20111201

Title: Membrane interaction and antibacterial properties of two mildly cationic peptide diastereomers, bombinins H2 and H4, isolated from Bombina skin.

Journal: European biophysics journal : EBJ 20110401

Title: The potential of antimicrobial peptides as biocides.

Journal: International journal of molecular sciences 20110101

Title: Total synthesis of the bicyclic depsipeptide HDAC inhibitors spiruchostatins A and B, 5''-epi-spiruchostatin B, FK228 (FR901228) and preliminary evaluation of their biological activity.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20091026

Title: Molecular aggregation in selected crystalline 1:1 complexes of hydrophobic D- and L-amino acids. IV. The L-phenylalanine series.

Journal: Acta crystallographica. Section C, Crystal structure communications 20090601

Title: Folding propensity and biological activity of peptides: the effect of a single stereochemical isomerization on the conformational properties of bombinins in aqueous solution.

Journal: Biopolymers 20080901

Title: Second-tier test for quantification of alloisoleucine and branched-chain amino acids in dried blood spots to improve newborn screening for maple syrup urine disease (MSUD).

Journal: Clinical chemistry 20080301

Title: Stereoselective incorporation of isoleucine into Cypridina luciferin in Cypridina hilgendorfii (Vargula hilgendorfii).

Journal: Bioscience, biotechnology, and biochemistry 20060601

Title: In vitro quantification of hydrolysis-induced racemization of amino acid enantiomers in environmental samples using deuterium labeling and electron-impact ionization mass spectrometry.

Journal: Analytical chemistry 20020701

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