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Quality Control of N-Me-Leu-OH Purity: 98% SDS Specification

COA

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NMR

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CNMR

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HPLC

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Product Citations

Antimycobacterial Rufomycin Analogues from Streptomyces atratus Strain MJM3502

Zhou, Bin ; Shetye, Gauri ; Yu, Yang ; Santarsiero, Bernard D. ; Klein, Larry L. ; Abad-Zapatero, Cele , et al.

DOI: 10.1021/acs.jnatprod.9b01095 PubMed ID: 32031795 J. Nat. Prod.,2020,83(3):657-667.

Abstract: This study represents a systematic chem. and biol. study of the rufomycin (RUF) class of cyclic heptapeptides, which our anti-TB drug discovery efforts have identified as potentially promising anti-TB agents that newly target the caseinolytic protein C1, ClpC1. Eight new RUF analogs, rufomycins NBZ1-NBZ8, as well as 5 known peptides were isolated and characterized from the Streptomyces atratus strain MJM3502. Advanced Marfey's and X-ray crystallog. anal. led to the assignment of the absolute configuration of the RUFs. Several isolates exhibited potent activity against both pathogens M. tuberculosis H37Rv and M. abscessus, paired with favorable selectivity (selectivity index >60), which collectively underscores the promise of the rufomycins as potential anti-TB drug leads.

Purchased from AmBeed: 61-90-5 ; 3060-46-6 ; 56-41-7 ; 621-44-3

Product Details of N-Me-Leu-OH

CAS No. :	3060-46-6
Formula :	C₇H₁₅NO₂
M.W :	145.20
SMILES Code :	CC(C)C[C@H](NC)C(O)=O
MDL No. :	MFCD00065919
InChI Key :	XJODGRWDFZVTKW-LURJTMIESA-N
Pubchem ID :	2777993

Safety of N-Me-Leu-OH

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of N-Me-Leu-OH

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 3060-46-6 ]

[ 3060-46-6 ] Synthesis Path-Downstream 1~35

1
[ 50-00-0 ]
[ 61-90-5 ]
[ 3060-46-6 ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 7680 - 7682.
[2]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1946,vol. 66,p. 6.
Chem.Abstr.,1951,p. 7957.

2
[ 3060-46-6 ]
[ 70-34-8 ]
[ 69935-32-6 ]

References: [1]Helvetica Chimica Acta,1948,vol. 31,p. 2200.

3
[ 674-82-8 ]
[ 3060-46-6 ]
[ 35141-03-8 ]

References: [1]Journal of Organic Chemistry,1972,vol. 37,p. 3265 - 3268.

4
[ 67-56-1 ]
[ 3060-46-6 ]
[ 35026-08-5 ]

References: [1]Bulletin of the Chemical Society of Japan,1973,vol. 46,p. 231 - 237.
[2]ACS Chemical Neuroscience,2013,vol. 4,p. 1204 - 1216.

5
[ 3060-46-6 ]
[ 89941-16-2 ]

References: [1]Helvetica Chimica Acta,1964,vol. 47,p. 166 - 173.

6
[ 60643-14-3 ]
[ 3060-46-6 ]

References: [1]Helvetica Chimica Acta,1963,vol. 46,p. 327 - 333.

7
Sporidesmolsaeure C; L-α-Hydroxy-isocaproyl-Val-N-methyl-Leu [ No CAS ]
[ 3060-46-6 ]

References: [1]Journal of the Chemical Society C: Organic,1967,p. 634 - 638.

8
[ 3060-46-6 ]
[ 4457-32-3 ]
[ 4216-95-9 ]

References: [1]Journal of general chemistry of the USSR,1972,vol. 42,p. 2316 - 2328.
Zhurnal Obshchei Khimii,1972,vol. 42,p. 2320 - 2334.

9
[ 3060-46-6 ]
[ 69146-58-3 ]
[ 141849-38-9 ]

References: [1]Journal of the American Chemical Society,1992,vol. 114,p. 6661 - 6671.

10
[ 3060-46-6 ]
[ 10203-89-1 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1981,vol. 100,p. 204 - 207.

11
[ 64143-85-7 ]
[ 3060-46-6 ]

References: [1]Collection of Czechoslovak Chemical Communications,1988,vol. 53,p. 2473 - 2494.

12
(S)-2-(2-Aza-bicyclo[2.2.1]hept-5-en-2-yl)-4-methyl-pentanoic acid [ No CAS ]
[ 3060-46-6 ]
[ 542-92-7 ]

References: [1]Journal of Organic Chemistry,1987,vol. 52,p. 5746 - 5749.

13
(2S,2'S)-N-<2'-(methylamino)-4'-methylpentanoyl>bornane-10,2-sultam [ No CAS ]
[ 3060-46-6 ]

References: [1]Helvetica Chimica Acta,1993,vol. 76,p. 187 - 196.
[2]Helvetica Chimica Acta,1993,vol. 76,p. 187 - 196.

14
[ 3060-46-6 ]
[ 79-04-9 ]
[ 138062-83-6 ]

References: [1]Angewandte Chemie,1992,vol. 104,p. 222 - 224.

15
Cyclosporin L [ No CAS ]
[ 72-18-4 ]
[ 2480-23-1 ]
[ 3060-46-6 ]
(2s)-2-Amino-2-<(2R,3R)-5-ethyl-2,3,4,5-tetrahydro-3-methylfuryl>essigsaeure [ No CAS ]

References: [1]Helvetica Chimica Acta,1987,vol. 70,p. 13 - 36.

16
Cyclosporin Z [ No CAS ]
[ 72-18-4 ]
[ 2480-23-1 ]
[ 3060-46-6 ]
N-Methyl-L-2-aminooctansaeure [ No CAS ]

References: [1]Helvetica Chimica Acta,1987,vol. 70,p. 13 - 36.

17
[ 3060-46-6 ]
[ 407-25-0 ]
[ 74530-79-3 ]

References: [1]Liebigs Annalen der Chemie,1980,p. 611 - 621.

18
[ 3060-46-6 ]
[ 115-11-7 ]
[ 42807-86-3 ]

References: [1]Liebigs Annalen der Chemie,1982,p. 2068 - 2078.

19
[ 66866-66-8 ]
[ 3060-46-6 ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 1985 - 1986.

Yield	Reaction Conditions	Operation in experiment
		The following can be prepared in a similar way: (S)-Z-N-Methylglycine, (S)-Z-N-methylalanine, (S)-Z-N-methyl-S-benzylcysteine; (S)-Z-N-methylleucine, (S)-Z-N-methylmethionine, (S)-Z-N-methyl-O-benzylthreonine.
0.85 g (46%)		methyl-L-leucine (NPC 15273) A suspension of N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-leucine (1.67 g, 5 mmol) in toluene(100 ml) was charged with paraformaldehyde (1 g, 33.3 mmol) and 4-toluenesulfonic acid (100 mg, catalytic). The mixture was refluxed for 30 minutes in a Dean Stark apparatus for azeotropic distillation. The solution was washed with a saturated solution of sodium bicarbonate (*2), dried over magnesium sulfate and evaporated. The resulting oil in a 1:1 mixture of chloroform:trifluoroacetic acid (50 ml), at room temperature, was charged with triethylsilane (2.38 ml, 15 mmol). Stirring was continued for 22 hr. The solvents were removed in vacuum and the oil was crystallized from a mixture of ether:hexane. Recrystalyzation from EtOAc:hexane afforded 0.85 g (46%) of the product as a colorless solid, mp 101-3 C.
		Characterising data Physical and spectral properties of MM 45289 after drying over P2O5: FAB-MS (glycerol/thioglycerol/trifluoroacetic acid) MH+1557+-1 Molecular Weight: 1556 Molecular Formula: C73H89N10O26Cl UV (H2O) lambdamax280 nm (epsilon 6215) [alpha]D20 -118 (c = 0.97% in H2O) IR (kBr) 1660, 1590, 1500, 1070 cmmin1 1H NMR in DMSO d6 at 358K. Tetramethylsilane as internal standard. deltaH 8.45 (1H, broad s), 8.23 (1H, br d, J ca.5Hz), 7.95 (1H, br d, J ca.5Hz), 7.63 (1H, d, J 8.0Hz), 7.52 (1H, d, J 8.3Hz), 7.39 (1H, s), 7.33 (1H, br d), 7.23 (1H, d, J 8.3Hz), 7.12 (1H, s), 7.1 (1H, br d), 6.97 (1H, d, J 8.0Hz), 6.76 (1H, dd, J 8.4 and 2.0Hz), 6.68 (1H, d, J 8.4Hz), 6.45 (1H, d, J 2.0Hz), 6.33 (1H, d, J 2.0Hz), 5.68 (1H, br), 5.63 (1H, s), 5.50 (1H, d, J 7.4Hz), 5.43 (1H, s), 5.27 (2H, overlapping), 5.13 (1H, d, J ca.2Hz), 4.70 (2H, overlapping), 4.50 (1H, d, J 6Hz), 4.47 (1H, d, J 6.1), 4.33 (1H, br), 4.21 (1H, br), 4.13 (1H, dq, J 6.0 and 9.6Hz), 3.75 - 3.30 (7H, overlapping), 3.00 (1H, dd, J 7.8 and 5.8Hz) 2.88 (1H, d, J 9.6Hz), 2.86 (lH, d, J 9.6Hz), 2.58 (lH, dd, J 15.8 and 4.0Hz), 2.32 (3H, s), 2.17 (lH, dd, 15.8 and 6.8Hz), 1.90 (1H, br d, J ca.13Hz), 1.82 (1H, d, J 13.7Hz), 1.77 (1H, m), 1.60 (2H, overlapping, J 13.5 and 4.4Hz), 1.52 (1H, m), 1.42 (1H, m), 1.18 (3H, d, J 5.9Hz), 1.13 (6H, s), 1.09 (3H, d, J 6.0Hz), 0.92 (3H, d, J 6.6Hz), 0.89 (3H, d, J 6.6Hz) ppm. Acid Hydrolysis (6MHCl/110/18hrs/N2/sealed tube) gives aspartic acid and N-methyl leucine. Physical and spectral data on MM 47756: FAB-Ms (thioglycerol/glycerol) MH+ 1523+-1 Molecular Weight: 1522 Molecular Formula: C73H90N10O26 1H NMR in DMSO d6 at 353K, Tetramethylsilane as internal standard. Inter alia 7.61 (2H, d, J ca.8.0Hz), 7.4 - 7.2 (3H, overlapping m), 7.13 (1H, dd, J 8.0 and 2.0Hz), 7.10 (1H, d, J 2.0 Hz), 7.07 (1H, dd, J 8.0 and 2.0Hz), 6.97 (1H, dd, J 8.0 and 2.0Hz), 6.76 (1H, dd, J 8.5 and 2.0Hz), 6.68 (1H, d, J 8.5Hz), 6.40 (1H, d, J 2.2Hz), 6.35 (1H, d, J 2.2Hz) ppm.

The following compounds can be prepared in a similar way: (S)-Z-N-Methylalanine; (R)-Z-N-Methylalanine; (+/-)-Z-N-Methylalanine; (S)-Z-N-Methylleucine; (R)-Z-N-Methylleucine; (+/-)-Z-N-Methylleucine; Z-N-Methylglycine; ...

22
[ 74-89-5 ]
d-α-bromo-isocaproic acid [ No CAS ]
[ 3060-46-6 ]

References: [1]Chemische Berichte,1916,vol. 49,p. 1359.

23
N-p-toluenesulfonyl-N-methyl-L-leucine methyl ester [ No CAS ]
[ 3060-46-6 ]

References: [1]Journal of Biological Chemistry,1944,vol. 155,p. 421,436.

24
p-toluenesulfonyl-methyl-l-leucine [ No CAS ]
[ 3060-46-6 ]

References: [1]Chemische Berichte,1915,vol. 48,p. 374.
[2]Chemische Berichte,1915,vol. 48,p. 374.

25
[ 3060-46-6 ]
L-amino acid oxide ase [ No CAS ]
[ 816-66-0 ]
[ 74-89-5 ]

References: [1]Journal of Biological Chemistry,1944,vol. 155,p. 421,436.

26
[ 7647-01-0 ]
[ 64143-96-0 ]
[ 3060-46-6 ]
[ 104-15-4 ]

References: [1]Chemische Berichte,1915,vol. 48,p. 374.

27
[ 10034-85-2 ]
[ 64143-96-0 ]
phosphonium iodide [ No CAS ]
[ 3060-46-6 ]
[ 106-45-6 ]

References: [1]Chemische Berichte,1915,vol. 48,p. 374.

28
[ 3060-46-6 ]
[ 62120-85-8 ]
[ 42417-80-1 ]

References: [1]Russian Journal of Bioorganic Chemistry,1999,vol. 25,p. 283 - 287.
Bioorganicheskaya Khimiya,1999,vol. 25,p. 323 - 328.

29
[ 278175-37-4 ]
[ 3060-46-6 ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 3034 - 3041.

30
[ 3060-46-6 ]
[ 100-51-6 ]
[ 48168-99-6 ]