Design of peptides with α,β-de­hydro residues: pseudo-tripeptide N-benzyl­oxy­carbonyl–ΔLeu–l-Ala–l-Leu–OCH3

Makker, J.; Dey, S.; Kumar, P.; Singh, T.P.

doi:10.1107/S0108270101016468

Design of peptides with α,β-dehydro residues: pseudo-tripeptide N-benzyloxycarbonyl–ΔLeu–L-Ala–L-Leu–OCH₃

J. Makker, S. Dey, P. Kumar and T. P. Singh

The title peptide N-benzyloxycarbonyl–ΔLeu–L-Ala–L-Leu–OCH₃ [methyl N-(benzyloxycarbonyl)-α,β-dehydroleucyl-L-alanyl-L-leucinate], C₂₄H₃₅N₃O₆, was synthesized in the solution phase. The peptide adopts a type II′ β-turn conformation which is stabilized by an intramolecular 4 $\rightarrow$ 1 N—H

O hydrogen bond. The crystal packing is stabilized by two intermolecular N—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101016468/de1174sup1.cif Contains datablocks global, III
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270101016468/de1174IIIsup2.hkl Contains datablock III

CCDC reference: 184489

Computing details top

Data collection: SDP (Enraf-Nonius, 1979); cell refinement: SDP; data reduction: SDP; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTON-(C) (Spek, 1999); software used to prepare material for publication: SHELXL97.

methyl N-(benzyloxycarbonyl)-α,β-dehydroleucyl-L-alanyl-L-leucinate top

Crystal data top

C₂₄H₃₅N₃O₆	F(000) = 496
M_r = 461.55	D_x = 1.185 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54180 Å
a = 10.2550 (15) Å	Cell parameters from 25 reflections
b = 9.5090 (14) Å	θ = 0–25°
c = 13.4550 (14) Å	µ = 0.70 mm⁻¹
β = 99.715 (11)°	T = 293 K
V = 1293.9 (3) Å³	Prism, colourless
Z = 2	0.3 × 0.2 × 0.1 mm

Data collection top

Enraf-Nonius CAD-4 diffractometer	2363 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.051
Graphite monochromator	θ_max = 75.0°, θ_min = 3.3°
ω–2θ scans	h = 0→12
Absorption correction: empirical (using intensity measurements) via ψ scans (SDP; enraf-Nonius, 1979)	k = 0→11
T_min = 0.845, T_max = 0.932	l = −16→16
2887 measured reflections	3 standard reflections every 60 min
2731 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.053	H-atom parameters constrained
wR(F²) = 0.154	Calculated w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
S = 1.14	(Δ/σ)_max = 0.001
2731 reflections	Δρ_max = 0.20 e Å⁻³
298 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.0 (4)

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	1.0337 (4)	0.3539 (4)	−0.3469 (3)	0.0555 (9)
C2	1.0353 (6)	0.3454 (10)	−0.4489 (4)	0.105 (2)
H02A	0.9741	0.2884	−0.4890	0.080*
C3	1.1259 (7)	0.4199 (13)	−0.4922 (5)	0.137 (4)
H03A	1.1219	0.4165	−0.5618	0.080*
C4	1.2196 (6)	0.4972 (8)	−0.4360 (5)	0.098 (2)
H04A	1.2815	0.5458	−0.4661	0.080*
C5	1.2236 (5)	0.5041 (7)	−0.3350 (4)	0.0828 (14)
H05A	1.2886	0.5572	−0.2952	0.080*
C6	1.1305 (5)	0.4315 (6)	−0.2908 (4)	0.0741 (12)
H06A	1.1345	0.4363	−0.2213	0.080*
C0	0.9304 (4)	0.2747 (4)	−0.3027 (3)	0.0559 (9)
H0A	0.8445	0.3185	−0.3227	0.080*
H0B	0.9251	0.1785	−0.3270	0.080*
O0	0.9661 (2)	0.2765 (3)	−0.19625 (19)	0.0536 (6)
C0P	0.8808 (3)	0.2181 (4)	−0.1426 (3)	0.0447 (7)
O0P	0.7806 (3)	0.1559 (3)	−0.1800 (2)	0.0576 (7)
N1	0.9214 (3)	0.2367 (3)	−0.0443 (2)	0.0469 (6)
H1	0.9948	0.2799	−0.0242	0.080*
C1A	0.8470 (3)	0.1873 (3)	0.0278 (2)	0.0423 (7)
C1B	0.8288 (3)	0.2611 (4)	0.1076 (3)	0.0495 (8)
H1B	0.7776	0.2181	0.1498	0.080*
C1G	0.8801 (4)	0.4056 (5)	0.1393 (3)	0.0631 (11)
H1G	0.9437	0.4343	0.0963	0.080*
C1D1	0.7723 (6)	0.5110 (6)	0.1297 (6)	0.106 (2)
H1DA	0.7269	0.5133	0.0612	0.080*
H1DB	0.8089	0.6020	0.1483	0.080*
H1DC	0.7111	0.4858	0.1734	0.080*
C1D2	0.9496 (8)	0.3989 (8)	0.2458 (6)	0.126 (3)
H1DE	0.9831	0.4904	0.2668	0.080*
H1DF	1.0217	0.3334	0.2509	0.080*
H1DG	0.8887	0.3685	0.2884	0.080*
C1P	0.7996 (3)	0.0383 (3)	0.0141 (2)	0.0370 (6)
O1P	0.8716 (2)	−0.0545 (3)	−0.0075 (2)	0.0548 (6)
N2	0.6746 (2)	0.0154 (2)	0.02715 (18)	0.0353 (5)
H2	0.6262	0.0858	0.0380	0.080*
C2A	0.6189 (3)	−0.1252 (3)	0.0234 (3)	0.0415 (7)
H2A	0.6920	−0.1897	0.0474	0.080*
C2B	0.5197 (5)	−0.1381 (5)	0.0964 (3)	0.0640 (10)
H2BA	0.5606	−0.1076	0.1623	0.080*
H2BB	0.4924	−0.2344	0.0995	0.080*
H2BC	0.4438	−0.0804	0.0731	0.080*
C2P	0.5595 (3)	−0.1716 (3)	−0.0811 (2)	0.0394 (6)
O2P	0.4962 (3)	−0.2825 (3)	−0.0942 (2)	0.0570 (7)
N3	0.5801 (3)	−0.0937 (3)	−0.1602 (2)	0.0439 (6)
H3	0.6163	−0.0121	−0.1508	0.080*
C3A	0.5411 (4)	−0.1476 (4)	−0.2609 (3)	0.0521 (8)
H3A	0.4460	−0.1673	−0.2710	0.080*
C3B	0.5656 (4)	−0.0376 (5)	−0.3389 (3)	0.0564 (9)
H3BA	0.6545	−0.0005	−0.3200	0.080*
H3BB	0.5605	−0.0831	−0.4040	0.080*
C3G	0.4683 (5)	0.0835 (6)	−0.3490 (4)	0.0743 (13)
H3G	0.4551	0.1105	−0.2811	0.080*
C3D1	0.5232 (6)	0.2101 (7)	−0.3970 (5)	0.0953 (17)
H3DA	0.6076	0.2351	−0.3586	0.080*
H3DB	0.4633	0.2879	−0.3978	0.080*
H3DC	0.5333	0.1875	−0.4648	0.080*
C3D2	0.3372 (6)	0.0468 (12)	−0.4082 (6)	0.134 (3)
H3DD	0.2799	0.1271	−0.4121	0.080*
H3DE	0.2993	−0.0293	−0.3758	0.080*
H3DF	0.3477	0.0188	−0.4749	0.080*
C3P	0.6128 (6)	−0.2843 (5)	−0.2761 (4)	0.0733 (12)
O3P	0.5610 (6)	−0.3727 (4)	−0.3336 (3)	0.1158 (17)
O4T	0.7289 (3)	−0.2928 (4)	−0.2203 (4)	0.0976 (13)
C4T	0.7992 (8)	−0.4215 (8)	−0.2269 (8)	0.152 (4)
H4TA	0.8830	−0.4172	−0.1826	0.080*
H4TB	0.8134	−0.4350	−0.2950	0.080*
H4TC	0.7484	−0.4985	−0.2076	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.064 (2)	0.0466 (19)	0.059 (2)	0.0080 (17)	0.0176 (16)	0.0106 (16)
C2	0.101 (4)	0.154 (7)	0.056 (3)	−0.036 (4)	0.005 (2)	0.013 (3)
C3	0.128 (5)	0.221 (11)	0.061 (3)	−0.051 (7)	0.018 (3)	0.030 (5)
C4	0.094 (4)	0.111 (5)	0.099 (4)	−0.004 (4)	0.045 (3)	0.038 (4)
C5	0.082 (3)	0.081 (4)	0.091 (3)	−0.016 (3)	0.030 (3)	0.001 (3)
C6	0.090 (3)	0.072 (3)	0.065 (2)	−0.019 (3)	0.028 (2)	−0.009 (2)
C0	0.071 (2)	0.0427 (18)	0.0544 (19)	−0.0043 (17)	0.0129 (17)	0.0008 (16)
O0	0.0565 (12)	0.0543 (15)	0.0518 (12)	−0.0145 (12)	0.0145 (10)	0.0001 (11)
C0P	0.0465 (15)	0.0323 (14)	0.0564 (17)	−0.0035 (13)	0.0118 (12)	0.0014 (13)
O0P	0.0584 (13)	0.0552 (16)	0.0565 (14)	−0.0147 (12)	0.0022 (11)	0.0012 (12)
N1	0.0431 (12)	0.0450 (16)	0.0547 (15)	−0.0158 (12)	0.0144 (11)	−0.0033 (12)
C1A	0.0364 (13)	0.0386 (16)	0.0533 (17)	−0.0057 (12)	0.0111 (12)	0.0015 (13)
C1B	0.0441 (15)	0.0477 (19)	0.0605 (19)	−0.0139 (15)	0.0194 (13)	−0.0101 (16)
C1G	0.064 (2)	0.055 (2)	0.077 (2)	−0.0290 (19)	0.0310 (19)	−0.0214 (19)
C1D1	0.097 (4)	0.051 (3)	0.162 (6)	−0.013 (3)	0.002 (4)	−0.020 (3)
C1D2	0.132 (5)	0.076 (4)	0.148 (6)	−0.016 (4)	−0.039 (5)	−0.030 (4)
C1P	0.0349 (12)	0.0319 (14)	0.0448 (14)	0.0048 (12)	0.0084 (10)	0.0040 (12)
O1P	0.0452 (12)	0.0405 (13)	0.0822 (17)	0.0134 (10)	0.0208 (11)	0.0039 (12)
N2	0.0392 (11)	0.0209 (11)	0.0468 (12)	0.0000 (9)	0.0102 (9)	−0.0003 (9)
C2A	0.0447 (14)	0.0225 (13)	0.0587 (18)	−0.0025 (11)	0.0125 (13)	0.0055 (12)
C2B	0.085 (3)	0.055 (2)	0.057 (2)	−0.027 (2)	0.0267 (18)	−0.0005 (17)
C2P	0.0392 (13)	0.0249 (13)	0.0568 (17)	−0.0030 (11)	0.0159 (12)	−0.0001 (12)
O2P	0.0629 (14)	0.0383 (13)	0.0738 (16)	−0.0213 (12)	0.0226 (12)	−0.0065 (12)
N3	0.0535 (14)	0.0278 (12)	0.0511 (15)	−0.0077 (11)	0.0108 (11)	−0.0009 (10)
C3A	0.0612 (19)	0.0439 (18)	0.0517 (19)	−0.0138 (16)	0.0111 (15)	−0.0056 (15)
C3B	0.064 (2)	0.060 (2)	0.0464 (17)	−0.0099 (19)	0.0128 (15)	0.0015 (16)
C3G	0.082 (3)	0.083 (3)	0.059 (2)	0.016 (3)	0.017 (2)	0.014 (2)
C3D1	0.112 (4)	0.076 (4)	0.098 (4)	0.015 (3)	0.017 (3)	0.028 (3)
C3D2	0.079 (3)	0.180 (9)	0.137 (6)	0.000 (5)	0.004 (3)	0.077 (6)
C3P	0.104 (3)	0.043 (2)	0.079 (3)	−0.016 (2)	0.034 (2)	−0.017 (2)
O3P	0.190 (5)	0.059 (2)	0.098 (3)	−0.022 (3)	0.025 (3)	−0.039 (2)
O4T	0.075 (2)	0.060 (2)	0.162 (4)	0.0089 (18)	0.029 (2)	−0.034 (2)
C4T	0.140 (6)	0.069 (4)	0.265 (12)	0.035 (4)	0.087 (7)	−0.016 (6)

Geometric parameters (Å, º) top

C1—C6	1.359 (6)	C1P—N2	1.341 (4)
C1—C2	1.377 (6)	N2—C2A	1.451 (4)
C1—C0	1.502 (5)	N2—H2	0.8600
C2—C3	1.374 (9)	C2A—C2P	1.500 (5)
C2—H02A	0.9300	C2A—C2B	1.535 (5)
C3—C4	1.338 (11)	C2A—H2A	0.9800
C3—H03A	0.9300	C2B—H2BA	0.9600
C4—C5	1.355 (8)	C2B—H2BB	0.9600
C4—H04A	0.9300	C2B—H2BC	0.9600
C5—C6	1.391 (7)	C2P—O2P	1.235 (4)
C5—H05A	0.9300	C2P—N3	1.343 (4)
C6—H06A	0.9300	N3—C3A	1.441 (4)
C0—O0	1.417 (4)	N3—H3	0.8600
C0—H0A	0.9700	C3A—C3P	1.524 (6)
C0—H0B	0.9700	C3A—C3B	1.533 (5)
O0—C0P	1.345 (4)	C3A—H3A	0.9800
C0P—O0P	1.218 (4)	C3B—C3G	1.515 (7)
C0P—N1	1.329 (4)	C3B—H3BA	0.9700
N1—C1A	1.413 (4)	C3B—H3BB	0.9700
N1—H1	0.8600	C3G—C3D2	1.483 (9)
C1A—C1B	1.322 (5)	C3G—C3D1	1.518 (8)
C1A—C1P	1.500 (4)	C3G—H3G	0.9800
C1B—C1G	1.507 (5)	C3D1—H3DA	0.9600
C1B—H1B	0.9300	C3D1—H3DB	0.9600
C1G—C1D1	1.482 (8)	C3D1—H3DC	0.9600
C1G—C1D2	1.490 (8)	C3D2—H3DD	0.9600
C1G—H1G	0.9800	C3D2—H3DE	0.9600
C1D1—H1DA	0.9600	C3D2—H3DF	0.9600
C1D1—H1DB	0.9600	C3P—O3P	1.204 (6)
C1D1—H1DC	0.9600	C3P—O4T	1.298 (7)
C1D2—H1DE	0.9600	O4T—C4T	1.430 (7)
C1D2—H1DF	0.9600	C4T—H4TA	0.9600
C1D2—H1DG	0.9600	C4T—H4TB	0.9600
C1P—O1P	1.217 (4)	C4T—H4TC	0.9600

C6—C1—C2	117.0 (4)	C2A—N2—H2	119.2
C6—C1—C0	123.4 (4)	N2—C2A—C2P	113.5 (3)
C2—C1—C0	119.6 (4)	N2—C2A—C2B	110.5 (3)
C3—C2—C1	121.0 (6)	C2P—C2A—C2B	111.6 (3)
C3—C2—H02A	119.5	N2—C2A—H2A	106.9
C1—C2—H02A	119.5	C2P—C2A—H2A	106.9
C4—C3—C2	121.1 (6)	C2B—C2A—H2A	106.9
C4—C3—H03A	119.5	C2A—C2B—H2BA	109.5
C2—C3—H03A	119.5	C2A—C2B—H2BB	109.5
C3—C4—C5	119.4 (5)	H2BA—C2B—H2BB	109.5
C3—C4—H04A	120.3	C2A—C2B—H2BC	109.5
C5—C4—H04A	120.3	H2BA—C2B—H2BC	109.5
C4—C5—C6	119.9 (5)	H2BB—C2B—H2BC	109.5
C4—C5—H05A	120.1	O2P—C2P—N3	120.5 (3)
C6—C5—H05A	120.1	O2P—C2P—C2A	120.4 (3)
C1—C6—C5	121.5 (4)	N3—C2P—C2A	119.1 (3)
C1—C6—H06A	119.3	C2P—N3—C3A	119.6 (3)
C5—C6—H06A	119.3	C2P—N3—H3	120.2
O0—C0—C1	108.4 (3)	C3A—N3—H3	120.2
O0—C0—H0A	110.0	N3—C3A—C3P	111.5 (3)
C1—C0—H0A	110.0	N3—C3A—C3B	110.5 (3)
O0—C0—H0B	110.0	C3P—C3A—C3B	110.6 (3)
C1—C0—H0B	110.0	N3—C3A—H3A	108.0
H0A—C0—H0B	108.4	C3P—C3A—H3A	108.0
C0P—O0—C0	117.2 (3)	C3B—C3A—H3A	108.0
O0P—C0P—N1	125.2 (3)	C3G—C3B—C3A	113.5 (3)
O0P—C0P—O0	124.0 (3)	C3G—C3B—H3BA	108.9
N1—C0P—O0	110.9 (3)	C3A—C3B—H3BA	108.9
C0P—N1—C1A	121.6 (3)	C3G—C3B—H3BB	108.9
C0P—N1—H1	119.2	C3A—C3B—H3BB	108.9
C1A—N1—H1	119.2	H3BA—C3B—H3BB	107.7
C1B—C1A—N1	123.3 (3)	C3D2—C3G—C3B	113.1 (6)
C1B—C1A—C1P	120.9 (3)	C3D2—C3G—C3D1	109.0 (5)
N1—C1A—C1P	115.5 (3)	C3B—C3G—C3D1	110.8 (4)
C1A—C1B—C1G	128.5 (3)	C3D2—C3G—H3G	107.9
C1A—C1B—H1B	115.7	C3B—C3G—H3G	107.9
C1G—C1B—H1B	115.7	C3D1—C3G—H3G	107.9
C1D1—C1G—C1D2	109.9 (5)	C3G—C3D1—H3DA	109.5
C1D1—C1G—C1B	111.8 (3)	C3G—C3D1—H3DB	109.5
C1D2—C1G—C1B	108.7 (4)	H3DA—C3D1—H3DB	109.5
C1D1—C1G—H1G	108.8	C3G—C3D1—H3DC	109.5
C1D2—C1G—H1G	108.8	H3DA—C3D1—H3DC	109.5
C1B—C1G—H1G	108.8	H3DB—C3D1—H3DC	109.5
C1G—C1D1—H1DA	109.5	C3G—C3D2—H3DD	109.5
C1G—C1D1—H1DB	109.5	C3G—C3D2—H3DE	109.5
H1DA—C1D1—H1DB	109.5	H3DD—C3D2—H3DE	109.5
C1G—C1D1—H1DC	109.5	C3G—C3D2—H3DF	109.5
H1DA—C1D1—H1DC	109.5	H3DD—C3D2—H3DF	109.5
H1DB—C1D1—H1DC	109.5	H3DE—C3D2—H3DF	109.5
C1G—C1D2—H1DE	109.5	O3P—C3P—O4T	126.2 (5)
C1G—C1D2—H1DF	109.5	O3P—C3P—C3A	120.8 (5)
H1DE—C1D2—H1DF	109.5	O4T—C3P—C3A	113.0 (4)
C1G—C1D2—H1DG	109.5	C3P—O4T—C4T	116.1 (5)
H1DE—C1D2—H1DG	109.5	O4T—C4T—H4TA	109.5
H1DF—C1D2—H1DG	109.5	O4T—C4T—H4TB	109.5
O1P—C1P—N2	123.1 (3)	H4TA—C4T—H4TB	109.5
O1P—C1P—C1A	121.1 (3)	O4T—C4T—H4TC	109.5
N2—C1P—C1A	115.7 (3)	H4TA—C4T—H4TC	109.5
C1P—N2—C2A	121.6 (2)	H4TB—C4T—H4TC	109.5
C1P—N2—H2	119.2

C6—C1—C2—C3	−4.1 (11)	N1—C1A—C1P—N2	−137.2 (3)
C0—C1—C2—C3	178.0 (7)	O1P—C1P—N2—C2A	4.5 (4)
C1—C2—C3—C4	3.5 (15)	C1A—C1P—N2—C2A	−175.5 (3)
C2—C3—C4—C5	−1.2 (14)	C1P—N2—C2A—C2P	−87.2 (3)
C3—C4—C5—C6	−0.2 (11)	C1P—N2—C2A—C2B	146.5 (3)
C2—C1—C6—C5	2.7 (8)	N2—C2A—C2P—O2P	−172.2 (3)
C0—C1—C6—C5	−179.5 (5)	C2B—C2A—C2P—O2P	−46.5 (4)
C4—C5—C6—C1	−0.5 (9)	N2—C2A—C2P—N3	10.2 (4)
C6—C1—C0—O0	−9.7 (6)	C2B—C2A—C2P—N3	135.9 (3)
C2—C1—C0—O0	168.0 (5)	O2P—C2P—N3—C3A	−7.0 (5)
C1—C0—O0—C0P	175.9 (3)	C2A—C2P—N3—C3A	170.6 (3)
C0—O0—C0P—O0P	5.3 (5)	C2P—N3—C3A—C3P	−60.3 (4)
C0—O0—C0P—N1	−175.2 (3)	C2P—N3—C3A—C3B	176.3 (3)
O0P—C0P—N1—C1A	−1.9 (5)	N3—C3A—C3B—C3G	−73.0 (4)
O0—C0P—N1—C1A	178.7 (3)	C3P—C3A—C3B—C3G	163.1 (4)
C0P—N1—C1A—C1B	−137.8 (4)	C3A—C3B—C3G—C3D2	−77.1 (5)
C0P—N1—C1A—C1P	47.9 (4)	C3A—C3B—C3G—C3D1	160.1 (4)
N1—C1A—C1B—C1G	−0.4 (6)	N3—C3A—C3P—O3P	149.4 (5)
C1P—C1A—C1B—C1G	173.6 (4)	C3B—C3A—C3P—O3P	−87.3 (5)
C1A—C1B—C1G—C1D1	111.1 (5)	N3—C3A—C3P—O4T	−29.3 (5)
C1A—C1B—C1G—C1D2	−127.3 (5)	C3B—C3A—C3P—O4T	94.0 (5)
C1B—C1A—C1P—O1P	−131.6 (4)	O3P—C3P—O4T—C4T	−1.7 (9)
N1—C1A—C1P—O1P	42.8 (4)	C3A—C3P—O4T—C4T	177.0 (5)
C1B—C1A—C1P—N2	48.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1Pⁱ	0.86	2.08	2.904 (4)	159
N2—H2···O2Pⁱⁱ	0.86	2.01	2.848 (4)	165
N3—H3···O0P	0.86	2.40	3.181 (7)	151

Symmetry codes: (i) −x+2, y+1/2, −z; (ii) −x+1, y+1/2, −z.

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Design of peptides with α,β-de­hydro residues: pseudo-tripeptide N-benzyl­oxy­carbonyl–ΔLeu–L-Ala–L-Leu–OCH3

Supporting information

Design of peptides with α,β-dehydro residues: pseudo-tripeptide N-benzyloxycarbonyl–ΔLeu–L-Ala–L-Leu–OCH₃